Methanol → Methyl 5-chloro-2-fluorobenzoate

HRID 273115Notes

Reaction equation

HRID 273115 reaction equation
[CH3:1][OH:2].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([F:13])=[C:8]([CH:12]=1)[C:9](Cl)=[O:10]>ClCCl>[CH3:1][O:2][C:9](=[O:10])[C:8]1[CH:12]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=1[F:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 27736045-Chloro-2-fluorobenzoyl chloride

Product 1

HCID 21525433Methyl 5-chloro-2-fluorobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanol (20 ml) was added to a solution 5-chloro-2-fluoro-benzoyl chloride (1.2 g, 6.2 mmol) in dichloromethane (10 ml) in an ice-bath. The reaction mixture was warmed to room temperature, stirred for 3 h and then concentrated to afford 5-chloro-2-fluoro-benzoic acid methyl ester (1.17 g, 100%). 1H NMR (CDCl3), δ (ppm): 7.93 (m, 1H), 7.48 (m, 1H), 7.12 (m, 1H), 3.96 (s, 3H). Step 2: 5-Chloro-2-fluoro-benzoic acid hydrazide: A mixture of 5-chloro-2-fluoro-benzoic acid methyl ester (1.17 g, 6.2 mmol) and hydrazine monohydrate (0.451 ml, 9.3 mmol) in ethanol (20 ml) was stirred at room temperature overnight. The reaction mixture was concentrated and then the residue was triturated with diethyl ether to afford 5-chloro-2-fluoro-benzoic acid hydrazide (497 mg, 42%, white solid). 1H NMR (DMSO), δ (ppm): 9.66 (bs, 1H), 7.58 (m, 2H), 7.36 (m, 1H), 4.58 (bs, 2H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-739ce1068b2b404b9d2608b4179f615e
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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