Trimethylsilyldiazomethane → Methyl 4-(2-bromoacetyl)benzoate

HRID 1254021Notes

Reaction equation

HRID 1254021 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH3:14][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[Br:1][CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:14])=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-(Bromoacetyl)benzoic acid (10 g, 41.3 mmol) was dissolved in 75 mL of MeOH and 75 mL of methylene chloride. Trimethylsilyl diazomethane (2.0 M in ether) was slowly added at 0° C. until a yellow color persisted. The volatiles were evaporated to give the title compound. 1H NMR (500 MHz, (CD3OD): 8.18 (d, 2H), 8.16 (d, 2H), 4.68 (s, 2H), 3.96 (s, 3H). LCMS: m/z 258 (M+H)+.

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-6a3cd178274549faaebc179176750f47
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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