Boron tribromide → 3-Chloro-4-(3,3,3-trifluoro-2-hydroxy-2-isoquinolin-5-yl-1-methyl-propyl)-phenol

HRID 1095965Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:27])[C:11]([C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][N:21]=[CH:22]2)([OH:16])[C:12]([F:15])([F:14])[F:13].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:27])[C:11]([OH:16])([C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][N:21]=[CH:22]2)[C:12]([F:14])([F:13])[F:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(2-chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-isoquinolin-5-yl-butan-2-ol (50 mg) in dichloromethane (1.3 ml) was cooled to −70° C. A 1 M solution of boron tribromide in dichloromethane (0.505 ml) was added and the mixture was stirred at −70° C. for 30 min and at 0° C. for 1 h. A mixture of ice water and saturated aqueous NaHCO3 solution was added and the mixture was extracted with dichloromethane. The organic phase was washed with water and dried (MgSO4). The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1) to give the title compound (45 mg) as a colorless solid. MS (m/e)=382.1 [M+H+].

Workup

additionwas added
extractionthe mixture was extracted with dichloromethane
washThe organic phase was washed with water
dry with materialdried (MgSO4)
customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1)

Sources & evidence

ORD record: ord-78324c361af64426aa7889eb9fc1d8eb
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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