Hydrochloric Acid → 2-(2-Bromo-5-hydroxyphenyl)acetic acid

HRID 885266Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=C[C:3]=1CC#N.[OH-:12].[K+].Cl.[CH3:15][C:16]([OH:19])(C)[CH3:17]>>[Br:1][C:2]1[CH:3]=[CH:17][C:16]([OH:19])=[CH:15][C:7]=1[CH2:6][C:5]([OH:8])=[O:12]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 6386tert-Butanol

HCID 14797Potassium Hydroxide

HCID 544192022-(2-Bromo-5-hydroxyphenyl)acetonitrile

Product 1

HCID 572578212-(2-Bromo-5-hydroxyphenyl)acetic acid

Conditions

Temperature: 85 °C

Procedure

(2-Bromo-5-hydroxy-phenyl)-acetonitrile (1.4 g, 6.6 mmol) and potassium hydroxide (4.5 g, 78.9 mmol) were combined in tBuOH and stirred at 85° C. for 3 hours. Once no starting material was seen by analytical LCMS, the mixture was cooled to 0° C. and the pH was adjusted to pH 6 with 10% aqueous HCl. The solution was extracted with EtOAc to give the desired product as a colorless oil (1.5 g).

Workup

temperaturethe mixture was cooled to 0° C.
extractionThe solution was extracted with EtOAc

Sources & evidence

ORD record: ord-ec418387346b4c7590adfc4349a76e8e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

Loading…