Methanol → Methyl 5-chloro-2-fluorobenzoate

HRID 732026Notes

Reaction equation

HRID 732026 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-eabef2cecb1e4c239f7825f9b5e58e82
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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