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

HRID 1711632Notes

Reaction equation

HRID 1711632 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-61fa3add94804a1ab15007d273986b35
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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