IE42828B1 - Process for the preparation of 3-bromobenzaldehyde - Google Patents
Process for the preparation of 3-bromobenzaldehydeInfo
- Publication number
- IE42828B1 IE42828B1 IE1152/76A IE115276A IE42828B1 IE 42828 B1 IE42828 B1 IE 42828B1 IE 1152/76 A IE1152/76 A IE 1152/76A IE 115276 A IE115276 A IE 115276A IE 42828 B1 IE42828 B1 IE 42828B1
- Authority
- IE
- Ireland
- Prior art keywords
- benzaldehyde
- bromine
- chlorine
- mixture
- bromination
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 52
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 24
- 230000031709 bromination Effects 0.000 claims abstract description 22
- 238000005893 bromination reaction Methods 0.000 claims abstract description 22
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical class OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000007517 lewis acids Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB23771/75A GB1535333A (en) | 1975-06-02 | 1975-06-02 | Process for the preparation of 3-bromo-benzaldehyde |
| GB33076 | 1976-01-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42828L IE42828L (en) | 1976-12-02 |
| IE42828B1 true IE42828B1 (en) | 1980-10-22 |
Family
ID=26235853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1152/76A IE42828B1 (en) | 1975-06-02 | 1976-05-31 | Process for the preparation of 3-bromobenzaldehyde |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS51143639A (enExample) |
| BR (1) | BR7603452A (enExample) |
| CA (1) | CA1069135A (enExample) |
| CH (1) | CH620188A5 (enExample) |
| DD (1) | DD124377A5 (enExample) |
| DE (1) | DE2624410A1 (enExample) |
| DK (1) | DK238776A (enExample) |
| FR (1) | FR2313339A1 (enExample) |
| HU (1) | HU174975B (enExample) |
| IE (1) | IE42828B1 (enExample) |
| IL (1) | IL49688A (enExample) |
| IT (1) | IT1060880B (enExample) |
| LU (1) | LU75056A1 (enExample) |
| NL (1) | NL7605829A (enExample) |
| SU (1) | SU680641A3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3136561A1 (de) * | 1981-09-15 | 1983-03-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von para-substituierten 3-brombenzaldehyden |
| US4585898A (en) * | 1984-12-18 | 1986-04-29 | Hardwicke Chemical Company | Preparation of substituted benzaldehydes |
-
1976
- 1976-05-03 CA CA251,701A patent/CA1069135A/en not_active Expired
- 1976-05-31 DD DD193100A patent/DD124377A5/xx unknown
- 1976-05-31 DE DE19762624410 patent/DE2624410A1/de not_active Withdrawn
- 1976-05-31 BR BR3452/76A patent/BR7603452A/pt unknown
- 1976-05-31 IE IE1152/76A patent/IE42828B1/en unknown
- 1976-05-31 LU LU75056A patent/LU75056A1/xx unknown
- 1976-05-31 FR FR7616353A patent/FR2313339A1/fr active Granted
- 1976-05-31 HU HU76SE1836A patent/HU174975B/hu unknown
- 1976-05-31 JP JP51062450A patent/JPS51143639A/ja active Pending
- 1976-05-31 IL IL49688A patent/IL49688A/xx unknown
- 1976-05-31 DK DK238776A patent/DK238776A/da not_active Application Discontinuation
- 1976-05-31 IT IT23799/76A patent/IT1060880B/it active
- 1976-05-31 SU SU762363456A patent/SU680641A3/ru active
- 1976-05-31 NL NL7605829A patent/NL7605829A/xx not_active Application Discontinuation
- 1976-05-31 CH CH680876A patent/CH620188A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51143639A (en) | 1976-12-10 |
| AU1444576A (en) | 1977-12-08 |
| HU174975B (hu) | 1980-04-28 |
| IL49688A (en) | 1978-12-17 |
| BR7603452A (pt) | 1977-01-04 |
| DK238776A (da) | 1976-12-03 |
| IT1060880B (it) | 1982-09-30 |
| IL49688A0 (en) | 1976-07-30 |
| IE42828L (en) | 1976-12-02 |
| CH620188A5 (en) | 1980-11-14 |
| NL7605829A (nl) | 1976-12-06 |
| FR2313339B1 (enExample) | 1978-11-17 |
| FR2313339A1 (fr) | 1976-12-31 |
| LU75056A1 (enExample) | 1977-02-15 |
| CA1069135A (en) | 1980-01-01 |
| SU680641A3 (ru) | 1979-08-15 |
| DD124377A5 (enExample) | 1977-02-16 |
| DE2624410A1 (de) | 1976-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Castro et al. | Cupric halide halogenations | |
| Miller et al. | General indene synthesis via cyclization of phenyl-substituted allylic cations | |
| JPS6212212B2 (enExample) | ||
| Conte et al. | Iodofluorination of alkenes and alkynes promoted by iodine and 4-iodotoluene difluoride | |
| JP2618221B2 (ja) | 殺虫剤製造用中間体 | |
| Samuel et al. | Carbanionic rearrangements of halomethylenecycloalkanes | |
| US6956142B2 (en) | Process for eco-friendly synthesis of bromobenzene | |
| IE42828B1 (en) | Process for the preparation of 3-bromobenzaldehyde | |
| CN107641067B (zh) | 一种邻二酮的α位溴化方法 | |
| Uemura et al. | Stereochemistry of the bromination of acetylenes with bromine and copper (II) bromide | |
| He et al. | The photochemical synthesis of α, α, α-bromodifluorotoluene and α, α, α-chlorodifluorotoluene | |
| US3424804A (en) | Preparation of highly fluorinated aromatic compounds | |
| Sweet et al. | The reduction of acetylenic carbinols with titanium trichloride | |
| JP4257493B2 (ja) | 含フッ素アルキルハロゲン化物の製造方法 | |
| Cammidge et al. | Convenient ring-bromination of alkylnaphthalenes using N-bromosuccinimide in acetonitrile | |
| US6025528A (en) | Aqueous method to prepare cyclopropyl methylketone from acetyl-propanol | |
| Cardinale et al. | Reaction of alkoxyhydroperoxides with metal salts alkyl halide preparation | |
| JP2008174519A (ja) | テトラヒドロピランを溶媒とする対称ビフェニル化合物の製造方法 | |
| JP4403369B2 (ja) | フルオロフェノール誘導体の製造方法 | |
| McEwen et al. | Mechanism of the thermal decomposition of the condensation product of a phosphonium ylide with an epoxide | |
| Newman et al. | Synthesis of 4-bromophenanthrene | |
| KR810001279B1 (ko) | 메타-아릴옥시-벤즈알데히드류의 제조방법 | |
| JP2001039904A (ja) | ブロモアルキルナフタレンの製造方法 | |
| JPH08268990A (ja) | ７−メチル−２−ナフタレンカルボニトリルの製造方法 | |
| JP2009079024A (ja) | ２−ナフトール誘導体の製造方法 |