CA1069135A - Process for the preparation of 3-bromobenzaldehyde - Google Patents
Process for the preparation of 3-bromobenzaldehydeInfo
- Publication number
- CA1069135A CA1069135A CA251,701A CA251701A CA1069135A CA 1069135 A CA1069135 A CA 1069135A CA 251701 A CA251701 A CA 251701A CA 1069135 A CA1069135 A CA 1069135A
- Authority
- CA
- Canada
- Prior art keywords
- benzaldehyde
- bromine
- chlorine
- mixture
- solvent
- 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 abstract description 19
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 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 54
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 26
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 25
- 230000031709 bromination Effects 0.000 claims abstract description 23
- 238000005893 bromination reaction Methods 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- 239000000460 chlorine Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 229940095076 benzaldehyde Drugs 0.000 description 17
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 101000870345 Vasconcellea cundinamarcensis Cysteine proteinase 1 Proteins 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229940037003 alum Drugs 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids 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
- 238000011065 in-situ storage Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 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
- 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1069135A true CA1069135A (en) | 1980-01-01 |
Family
ID=26235853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,701A Expired CA1069135A (en) | 1975-06-02 | 1976-05-03 | Process for the preparation of 3-bromobenzaldehyde |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS51143639A (en:Method) |
| BR (1) | BR7603452A (en:Method) |
| CA (1) | CA1069135A (en:Method) |
| CH (1) | CH620188A5 (en:Method) |
| DD (1) | DD124377A5 (en:Method) |
| DE (1) | DE2624410A1 (en:Method) |
| DK (1) | DK238776A (en:Method) |
| FR (1) | FR2313339A1 (en:Method) |
| HU (1) | HU174975B (en:Method) |
| IE (1) | IE42828B1 (en:Method) |
| IL (1) | IL49688A (en:Method) |
| IT (1) | IT1060880B (en:Method) |
| LU (1) | LU75056A1 (en:Method) |
| NL (1) | NL7605829A (en:Method) |
| SU (1) | SU680641A3 (en:Method) |
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 CH CH680876A patent/CH620188A5/de not_active IP Right Cessation
- 1976-05-31 IE IE1152/76A patent/IE42828B1/en unknown
- 1976-05-31 FR FR7616353A patent/FR2313339A1/fr active Granted
- 1976-05-31 NL NL7605829A patent/NL7605829A/xx not_active Application Discontinuation
- 1976-05-31 DD DD193100A patent/DD124377A5/xx unknown
- 1976-05-31 DE DE19762624410 patent/DE2624410A1/de not_active Withdrawn
- 1976-05-31 HU HU76SE1836A patent/HU174975B/hu unknown
- 1976-05-31 IT IT23799/76A patent/IT1060880B/it active
- 1976-05-31 IL IL49688A patent/IL49688A/xx unknown
- 1976-05-31 DK DK238776A patent/DK238776A/da not_active Application Discontinuation
- 1976-05-31 LU LU75056A patent/LU75056A1/xx unknown
- 1976-05-31 BR BR3452/76A patent/BR7603452A/pt unknown
- 1976-05-31 SU SU762363456A patent/SU680641A3/ru active
- 1976-05-31 JP JP51062450A patent/JPS51143639A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1060880B (it) | 1982-09-30 |
| LU75056A1 (en:Method) | 1977-02-15 |
| DK238776A (da) | 1976-12-03 |
| HU174975B (hu) | 1980-04-28 |
| IE42828B1 (en) | 1980-10-22 |
| JPS51143639A (en) | 1976-12-10 |
| CH620188A5 (en) | 1980-11-14 |
| BR7603452A (pt) | 1977-01-04 |
| DE2624410A1 (de) | 1976-12-16 |
| IL49688A0 (en) | 1976-07-30 |
| DD124377A5 (en:Method) | 1977-02-16 |
| NL7605829A (nl) | 1976-12-06 |
| IL49688A (en) | 1978-12-17 |
| AU1444576A (en) | 1977-12-08 |
| SU680641A3 (ru) | 1979-08-15 |
| FR2313339B1 (en:Method) | 1978-11-17 |
| IE42828L (en) | 1976-12-02 |
| FR2313339A1 (fr) | 1976-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |