4-(2-Bromoethyl)benzoic acid → Methyl 4-(2-bromoethyl)benzoate

HRID 491397Notes

Reaction equation

HRID 491397 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>ClCCl.CO.CCCCCC>[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 1040684-(2-Bromoethyl)benzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 10586287Methyl 4-(2-bromoethyl)benzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 4-(2-bromoethyl)benzoic acid (4.58 g, TCI) in a mixture of dichloromethane (50 ml) and methanol (50 ml) was added dropwise with a 2.0 M solution of (trimethylsilyl)diazomethane in hexane (11.0 ml, ALD) over 10 minutes, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and then the residue was purified by column chromatography (Flash, hexane:ethyl acetate=15:1) to obtain the title compound (Intermediate ia-01, 4.32 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (Flash, hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-214cfcc9646c4378ad79ca5184859c56
Source dataset
uspto-grants-2009_05
Patent number
US07531533B2

Reaction notes

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