Ethyl bromoacetate → (4-Acetyl-2-ethyl-3-hydroxy-phenoxy)-acetic acid ethyl ester

Reaction equation

[CH2:1]([C:3]1[C:4]([OH:13])=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[OH:9])[CH3:2].[CH2:14]([O:16][C:17](=[O:20])[CH2:18]Br)[CH3:15]>>[CH2:14]([O:16][C:17](=[O:20])[CH2:18][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[C:4]([OH:13])[C:3]=1[CH2:1][CH3:2])[CH3:15]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 212870211-(3-Ethyl-2,4-dihydroxyphenyl)ethanone

Product 1

HCID 67246312(4-Acetyl-2-ethyl-3-hydroxy-phenoxy)-acetic acid ethyl ester

Procedure

1-(3-Ethyl-2,4-dihydroxy-phenyl)-ethanone was treated with 2-bromo-acetic acid ethyl ester and processed as described in the synthesis of example 20a. Yield, 96.89%; mp, 74-75° C.; MS (CI): 267 (M++1).

Workup

customas described in the synthesis of example 20a
customYield
custommp, 74-75° C.

Sources & evidence

ORD record: ord-256836ddf67c4667953ad9803e137f18
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964628B2

Reaction notes

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