Water → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 1909685Notes

Reaction equation

C[O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.O>ClCCl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-(4-methoxy-phenoxy)-biphenyl (3.2 g, 11.6 mmol) in anhydrous dichloromethane (60 mL) at −78° C. was added borontribromide (1M solution in dichloromethane) (7.52 g, 30 mmol) over a period of 15 min. The reaction mixture was stirred at −78° C. for 1 h, warmed to rt and stirred at rt for 1 h. The mixture was cooled to 0-5° C. Cold water (125 mL) was added over a period of 10 min and the mixture was extracted with dichloromethane (250 mL). The organic layer was dried over anhydrous Na2SO4. The crude mixture was purified by silica gel flash chromatography to obtain the title product (375 mg, 12%).

Workup

temperaturewarmed to rt
stirringstirred at rt for 1 h
temperatureThe mixture was cooled to 0-5° C
extractionthe mixture was extracted with dichloromethane (250 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
customThe crude mixture was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-527331f01fbd476e8d5bedb7fe7e3542
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

Loading…