Sulfuric Acid → Methyl 3-(bromomethyl)benzoate

HRID 1838111Notes

Reaction equation

HRID 1838111 reaction equation
C1(C)C=CC=C(C(O)=O)C=1.S(=O)(=O)(O)O.[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=1)=[O:19].[Br:27]N1C(=O)CCC1=O>CO>[CH3:16][O:17][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][Br:27])[CH:21]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 74183-Methylbenzoic acidHCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 67184N-bromobutanimide

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This is prepared as follows: 3-Toluic acid is converted with methanol in the presence of sulfuric acid into 3-toluic acid methyl ester, which reacts with N-bromosuccinimide to give 3-bromomethyl-benzoic acid methyl ester. Reaction of bromomethyl-benzoic acid methyl ester with triphenylphosphane finally leads to 3-(benzoic acid methyl ester)-methyltriphenylphosphonium bromide.

Workup

  1. customThis is prepared

Sources & evidence

ORD record
ord-340eac9a63fc461b8cf4403c0b636380
Source dataset
uspto-grants-2004_01
Patent number
US06673794B2

Reaction notes

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