2-Chlorophenol → Ethyl 2-(2-chlorophenoxy)acetate

HRID 2425016Notes

Reaction equation

HRID 2425016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:15]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by reacting 2-chloro-phenol, with ethyl 2-bromoacetate and K2CO3 in DMF. Yield, 97%, colourless oil; 1H NMR (CDCl3): 1.29 (3H, t, J=6.3, CH2CH3), 4.29 (2H, q, J=6.3, CH2CH3), 4.72 (2H, s, OCH2), 6.76 (1H, d, J=8.2, H-6), 6.95 (1H, m, H-4), 720 (1H, m, H-5), 7.40 (1H, dd, J=8.2, H-3).

Workup

  1. customYield

Sources & evidence

ORD record
ord-05587367395c47739e8519fe862b49e0
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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