Toluene → 3-Bromo-4-fluorobenzaldehyde

HRID 1702635Notes

Reaction equation

HRID 1702635 reaction equation
NC1C=CC=CC=1.C1(C)C=CC=CC=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:26])C(O)=O)=[CH:18][C:17]=1[Br:27]>ClC1C=CC=CC=1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:26])=[CH:18][C:17]=1[Br:27]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6115AnilineHCID 20526243HCID 20526243, compound

Product 1

HCID 1736043-Bromo-4-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

102.3 g (1.1 moles) of freshly distilled aniline were added dropwise to a mixture of 1,300 ml of toluene or chlorobenzene and 247 g of 4-fluoro-3-bromophenylglyoxylic acid at 70° to 80° C. The reaction mixture was then heated to the reflux temperature, and was stirred under reflux for a further 4 hours in order to bring the decarboxylation to completion. Thereafter, the solvent was stripped off in vacuo. 270 g (97% of theory) of the anil remained in the form of a colorless powder with a melting point of 45° to 47° C.

Workup

  1. temperatureThe reaction mixture was then heated to the reflux temperature
  2. temperatureunder reflux for a further 4 hours in order

Sources & evidence

ORD record
ord-6f4120e218d8420a82e5985ccf9c914b
Source dataset
uspto-grants-1982_09
Patent number
US04348538

Reaction notes

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