Hexane → Methyl 4-fluorosalicylate

HRID 644167Notes

Reaction equation

HRID 644167 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-fluorosalicylate

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 trimethylsilyldiazomethane (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 trimethylsilyldiazomethane solution (15 mL). The mixture was concentrated in vacuo to dryness to give 10.4 g of an oil which crystallized.

Workup

  1. concentrationThe mixture was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-3941a1030dbb4973b0b7d79e012589bb
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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