Hexane → Methyl 4-fluorosalicylate

HRID 1787888Notes

Reaction equation

HRID 1787888 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[CH3:12]CCCCC.C[Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 676614-Fluorosalicylic acidHCID 167693Trimethylsilyldiazomethane2×

Product 1

HCID 2775386Methyl 4-fluorosalicylateYield 98%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent2×

Procedure

A solution of 4-fluoro-2-hydroxybenzoic acid (9.8 g, 62.3 mmol) in benzene (100 mL) and MeOH (20 mL) was cooled in an ice bath and a 2 M hexane solution of (trimethyl-silyl)diazomethane (50 mL) was added dropwise. The reaction was stirred overnight at ambient temperature, diluted with benzene (348 mL) and MeOH (39 mL), and treated with more of the (trimethylsilyl)diazomethane solution (15 mL). The mixture was concentrated in vacuo to dryness to give the title compound (10.4 g, 98%) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-72635546d05941bc89539332989fdc4d
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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