Boron tribromide → 4'-Chloro-2'-methyl[1,1'-biphenyl]-2-ol

HRID 2116059Notes

Reaction equation

C[O:2][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH3:16])=[CH:5][CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:3]([OH:2])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[C:10]([CH3:16])[CH:11]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 689666184'-Chloro-2'-methyl-1,1'-biphenyl-2-yl methyl ether

Product 1

HCID 532185934'-Chloro-2'-methyl[1,1'-biphenyl]-2-olYield 97.5%

Procedure

Treatment of 2-bromo-5-chlorotoluene (5.0 g, 24.33 mmol) with 2-methoxybenzeneboronic acid (4.8 g, 31.63 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.478 g, 0.608 mmol), and potassium carbonate (8.41 g, 60.83 mmol) generally according to the procedure described for Intermediate 37 provided 5.05 g (89%) of 4′-chloro-2′-methyl-1,1′-biphenyl-2-yl methyl ether. Treatment of 4′-chloro-2′-methyl-1,1′-biphenyl-2-yl methyl ether (5.05 g, 21.48 mmol) with boron tribromide (5.37 g, 1.0 M in dichloromethane) generally according to the procedure described for Intermediate 163 provided 4.58 g (97%) of 4′-chloro-2′-methyl-1,1′-biphenyl-2-ol as a yellow oil. Anal. calcd. for C13H11ClO: C, 71.4; H, 5.07. Found: C, 71.03; H, 4.84.

Sources & evidence

ORD record: ord-aeb53d91919843a9b186c8b961f2d52e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

Loading…