Trimethylsilyldiazomethane → Methyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 14102Notes

Reaction equation

HRID 14102 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][OH:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][OH:12])[CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 81671273-Bromo-5-(hydroxymethyl)benzoic acid

Product 1

HCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To 3-bromo-5-(hydroxymethyl)benzoic acid (7.0 g, 30 mmol) in 20% methanol/benzene (100 mL) is added trimethylsilyldiazomethane (2M in hexanes), and the reaction is stirred 16 h. The reaction is concentrated under reduced pressure to afford the title compound. ESI MS m/z 244.0 [M+H]+.

Workup

  1. concentrationThe reaction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a362f1bc326742dc8cca9713458fb263
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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