3-Bromophenol → (3-bromophenoxy)acetic acid

HRID 1979071Notes

Reaction equation

HRID 1979071 reaction equation
BrC1C=C(O)C=CC=1.BrCC(OC)=O.[Br:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=1)[O:19][CH2:20][C:21]([O:23]C)=[O:22]>>[Br:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=1)[O:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 3

HCID 115633-Bromophenol2×HCID 60984Methyl bromoacetateHCID 13827038Acetic acid, 2-(3-bromophenoxy)-, methyl ester

Product 1

HCID 702285(3-bromophenoxy)acetic acid

Procedure

6-bromo-3-coumarone is prepared in four steps from commercial 3-bromophenol. The first step consists of an O-alkylation of the 3-bromophenol by methyl bromoacetate. The saponification of the methyl 3-bromophenoxyacetate allows one to obtain 3-bromophenoxyacetic acid, which is converted into the acid chloride by the action of thionyl chloride. This is subjected to an intramolecular Friedel Craft acylation to yield 6-bromo-3-coumarone.

Sources & evidence

ORD record
ord-3212bc45c4b24535aa5ed59a93f967c8
Source dataset
uspto-grants-2001_05
Patent number
US06239284B1

Reaction notes

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