Methyl chloroformate → 2-Chloro-4-fluoro-methoxycarbonyloxybenzene

HRID 2042052Notes

Reaction equation

HRID 2042052 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[OH:14].[OH-].[Na+]>O>[C:2](=[O:3])([O:4][CH3:5])[O:14][C:8]1[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=1[Cl:6]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 104884382-Chloro-4-fluoro-methoxycarbonyloxybenzeneYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl chloroformate (77.3 g, 0.82 mol) was added dropwise to a −10° C. solution of 2-chloro-4-fluorophenol (100 g, 0.68 mol) and sodium hydroxide (32.8 g, 0.82 mol) in water (550 mL). After complete addition, the precipitated solid was collected by filtration and washed with water to give 2-chloro-4-fluorophenyl methyl carbonate (110 g, 79% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.62 (dd, J=8.1, 2.7 Hz, 1H), 7.50 (dd, J=9.0, 5.4 Hz, 1H), 7.30 (td, J=8.1, 3.0 Hz, 1H), 3.86 (s, 3H); MS (ESI) m/z: 205.2 (M+H+).

Workup

  1. additionAfter complete addition
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-d3c40abd878d403e899c9ca6fa811692
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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