Boron tribromide → 2-(3-hydroxyphenyl)benzoic Acid

HRID 278167Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

2-(3-Methoxyphenyl)benzoic acid from Step B (6.53 g, 28.6 mmol) was dissolved in dry CH2Cl2 (100 mL) under argon and cooled to −78° C. Boron tribromide (62.9 mL of a 1.0 M solution in CH2Cl2, 62.9 mmol) was added dropwise and the solution was stirred overnight and allowed to warm slowly to ambient temperature. The resulting mixture was cooled in an ice bath and quenched carefully with water (200 mL), then extracted with CH2Cl2 (3×250 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the titled product which was sufficiently pure for use in the next step.

Workup

temperatureto warm slowly to ambient temperature
temperatureThe resulting mixture was cooled in an ice bath
customquenched carefully with water (200 mL)
extractionextracted with CH2Cl2 (3×250 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1998b0214d95455ea5bf5ae5fac151e2
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358985B1

Reaction notes

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