Boron tribromide → 3-Bromo-4-hydroxyphenylacetic acid

HRID 1622153Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 1366153-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 27696283-Bromo-4-hydroxyphenylacetic acidYield 91.1%

Procedure

Proceeding as in Reference 22, but substituting 3-bromo-4-methoxyphenylacetic acid (14.0 g, 0.057 mol) and boron tribromide (63 mL, 1M in dichloromethane, 0.063 mol), gave 3-bromo-4-hydroxyphenylacetic acid (12 g).

Sources & evidence

ORD record: ord-d822e89d77f643a5a8fe3d4f143e063b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778625B2

Reaction notes

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