Boron tribromide → 5-{2-[2-Chloro-4-(4-fluoro-3-hydroxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one

HRID 1095979Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16]C)[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:18]([CH3:33])[C:19]([C:25]1[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[CH:30]=1)([OH:24])[C:20]([F:23])([F:22])[F:21].B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([OH:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:18]([CH3:33])[C:19]([C:25]1[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[CH:30]=1)([OH:24])[C:20]([F:23])([F:21])[F:22]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 574213165-{2-[2-Chloro-4-(4-fluoro-3-methoxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one

Product 1

HCID 574213175-{2-[2-Chloro-4-(4-fluoro-3-hydroxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one

Procedure

In analogy to Example 147, step 5, 5-{2-[2-chloro-4-(4-fluoro-3-methoxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one was reacted with BBr3 to give the title compound as an off-white solid. MS (m/e)=472.2 [M+H+].

Sources & evidence

ORD record: ord-7f59ce37c4994559b954a9504c7d7451
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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