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

HRID 2386765Notes

Reaction equation

HRID 2386765 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:30])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][CH3:28])[C:21]=2[CH:29]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:30])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][CH3:28])[C:21]=2[CH:29]=1)([OH:16])[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 666972866-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 666973516-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-oneYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to Example 56, step 4, 6-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one (1.58 g) was reacted with 1M solution boron tribromide in dichloromethane, to give the title compound (1.57 g) as a light yellow solid. MS (m/e)=430.2 [M+H+].

Sources & evidence

ORD record
ord-fbaf02c8344d452ab5881047222169e2
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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