Boron tribromide → 4-Allyl-6-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4H-benzo[1,4]oxazin-3-one

HRID 2386779Notes

Reaction equation

HRID 2386779 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=3[Cl:25])[CH3:16])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:31])[CH:2]=[CH2:3].B(Br)(Br)Br>ClCCl>[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14]([OH:30])([C:26]([F:27])([F:29])[F:28])[CH:15]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=3[Cl:25])[CH3:16])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:31])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 675466024-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 666973894-Allyl-6-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4H-benzo[1,4]oxazin-3-oneYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to Example 56, step 4, 4-allyl-6-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4H-benzo[1,4]oxazin-3-one (2.5 g) was reacted with a 1M of solution boron tribromide in dichloromethane, to give the title compound (2.3 g) as a light yellow foam. MS (m/e)=442.3 [M+H+].

Sources & evidence

ORD record
ord-813dbbfffdec43ccbe64e14bc2d21326
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

Loading…