JPS6049609B2 - ｍ−ジハロゲノベンゼン類の塩素化方法 - Google Patents
ｍ−ジハロゲノベンゼン類の塩素化方法Info
- Publication number
- JPS6049609B2 JPS6049609B2 JP57168676A JP16867682A JPS6049609B2 JP S6049609 B2 JPS6049609 B2 JP S6049609B2 JP 57168676 A JP57168676 A JP 57168676A JP 16867682 A JP16867682 A JP 16867682A JP S6049609 B2 JPS6049609 B2 JP S6049609B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- amide
- formula
- dihalogenobenzenes
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 15
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 alkali metal amide Chemical class 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000000536 complexating effect Effects 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000003352 sequestering agent Substances 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000460 chlorine Substances 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 5
- 150000001768 cations Chemical class 0.000 abstract description 4
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 6
- 229910018954 NaNH2 Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 4
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- AJCSNHQKXUSMMY-UHFFFAOYSA-N 1-chloro-2,4-difluorobenzene Chemical compound FC1=CC=C(Cl)C(F)=C1 AJCSNHQKXUSMMY-UHFFFAOYSA-N 0.000 description 2
- OTZQYBFTOANOJO-UHFFFAOYSA-N 2-chloro-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Cl OTZQYBFTOANOJO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- NPXCSDPOOVOVDQ-UHFFFAOYSA-N 1,2-dichloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1Cl NPXCSDPOOVOVDQ-UHFFFAOYSA-N 0.000 description 1
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- XZGIHWAIIZHXKX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-n,n-bis[2-(2-ethoxyethoxy)ethyl]ethanamine Chemical compound CCOCCOCCN(CCOCCOCC)CCOCCOCC XZGIHWAIIZHXKX-UHFFFAOYSA-N 0.000 description 1
- MKIXXGAFSXWETQ-UHFFFAOYSA-N 2-butoxy-n,n-bis(2-butoxyethyl)ethanamine Chemical compound CCCCOCCN(CCOCCCC)CCOCCCC MKIXXGAFSXWETQ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR81.18585 | 1981-10-02 | ||
| FR8118585A FR2513991A1 (fr) | 1981-10-02 | 1981-10-02 | Procede de chloration de metadihalogenobenzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5874625A JPS5874625A (ja) | 1983-05-06 |
| JPS6049609B2 true JPS6049609B2 (ja) | 1985-11-02 |
Family
ID=9262686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57168676A Expired JPS6049609B2 (ja) | 1981-10-02 | 1982-09-29 | ｍ−ジハロゲノベンゼン類の塩素化方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4417081A (https=) |
| EP (1) | EP0076718B1 (https=) |
| JP (1) | JPS6049609B2 (https=) |
| AT (1) | ATE9320T1 (https=) |
| BR (1) | BR8205729A (https=) |
| CA (1) | CA1182844A (https=) |
| DE (1) | DE3260733D1 (https=) |
| FR (1) | FR2513991A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8716587D0 (en) * | 1987-07-14 | 1987-08-19 | Shell Int Research | Preparing thiophene derivatives |
| US5235020A (en) * | 1991-12-31 | 1993-08-10 | Amoco Corporation | Process for preparation of poly(aryl ether) polymers by acyclic catalysts |
| DE4445548A1 (de) * | 1994-12-20 | 1996-06-27 | Bayer Ag | Verfahren zur Herstellung von 3-Fluor-4,6-dichlortoluol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843637A (en) * | 1952-09-23 | 1958-07-15 | Ethyl Corp | Manufacture of tetrachlorobenzene |
| US4205014A (en) * | 1978-01-16 | 1980-05-27 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
| US4186153A (en) * | 1978-01-16 | 1980-01-29 | The Dow Chemical Company | Process for 1,2,4,5-tetrachlorobenzene |
-
1981
- 1981-10-02 FR FR8118585A patent/FR2513991A1/fr active Granted
-
1982
- 1982-09-20 AT AT82401695T patent/ATE9320T1/de not_active IP Right Cessation
- 1982-09-20 DE DE8282401695T patent/DE3260733D1/de not_active Expired
- 1982-09-20 EP EP82401695A patent/EP0076718B1/fr not_active Expired
- 1982-09-29 JP JP57168676A patent/JPS6049609B2/ja not_active Expired
- 1982-09-30 BR BR8205729A patent/BR8205729A/pt unknown
- 1982-09-30 US US06/428,451 patent/US4417081A/en not_active Expired - Fee Related
- 1982-10-01 CA CA000412663A patent/CA1182844A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2513991B1 (https=) | 1983-12-09 |
| CA1182844A (fr) | 1985-02-19 |
| EP0076718A1 (fr) | 1983-04-13 |
| EP0076718B1 (fr) | 1984-09-12 |
| ATE9320T1 (de) | 1984-09-15 |
| JPS5874625A (ja) | 1983-05-06 |
| BR8205729A (pt) | 1983-09-06 |
| FR2513991A1 (fr) | 1983-04-08 |
| DE3260733D1 (en) | 1984-10-18 |
| US4417081A (en) | 1983-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wiehn et al. | Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents | |
| US20070276168A1 (en) | Method For Preparation Of A Fluoroaromatic Compound From An Aminoaromatic Compound | |
| König et al. | Synthesis, structure, and reactivity of enediyne macrocycles | |
| JPH0788350B2 (ja) | Ｎ−フルオロスルホンアミドの製造方法 | |
| Gray et al. | Synthesis of specific polychlorinated dibenzofurans | |
| Correia | A triphasic brominating/oxidizing system | |
| WO2001081274A1 (fr) | Procede de fabrication d'un compose aromatique substitue | |
| Shou et al. | Synthesis and Reaction of Pentafluorosulfanyl Chloride (SF5Cl) | |
| JPS6049609B2 (ja) | ｍ−ジハロゲノベンゼン類の塩素化方法 | |
| Liu et al. | The mechanism of titanium complex-catalyzed reduction of aryl halides by sodium borohydride is strongly solvent dependent | |
| Lothian et al. | ipso-Fluorination of aryltrimethylsilanes using xenon difluoride | |
| EP0471755B1 (en) | N-fluoropyridinium pyridine heptafluorodiborate | |
| JP4612219B2 (ja) | 置換芳香族化合物の製造方法 | |
| EP0155093B1 (en) | Method for production of fluorine-containing aromatic derivative | |
| EP0119065B1 (en) | Process for preparing diaryls | |
| JPS6324980B2 (https=) | ||
| Bardin et al. | Fluorination of trimethylsilylfluoro-and trimethylsilyltetrafluorobenzenes with xenon difluoride | |
| Delaney et al. | Solvent effects in the chlorination of tetrahydrothiophens with N-chlorosuccinimide | |
| JPH0262832A (ja) | トリフルオロメチル誘導体の製造方法 | |
| Bardin et al. | Photoinduced Isomerization of Potassium Polyfluoroalk‐1‐enyltrifluoroborates | |
| Boudakian et al. | New synthesis routes to 2‐halopyridines. II. 2‐bromopyridine | |
| EP1201628B1 (en) | Electrophilic fluorination | |
| Naquib et al. | Kinetic study of the halogenation of imidazolidin-4-one derivatives | |
| Hartman et al. | Nucleophilic aromatic substitution by 3-amino-2-butenoates | |
| JP2543669B2 (ja) | 臭化パ―フルオロアルキルの製造方法 |