Tetramethylammonium fluoride → 6-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2096838Notes

Reaction equation

HRID 2096838 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:24])[C:9]([C:11]2[C:12]([F:23])=[CH:13][C:14]3[O:19][CH2:18][C:17](=[O:20])[N:16]([CH3:21])[C:15]=3[CH:22]=2)=[O:10])=[C:4]([Cl:25])[CH:3]=1.[F:26][C:27]([Si](C)(C)C)([F:29])[F:28].[F-].C[N+](C)(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:24])[C:9]([C:11]2[C:12]([F:23])=[CH:13][C:14]3[O:19][CH2:18][C:17](=[O:20])[N:16]([CH3:21])[C:15]=3[CH:22]=2)([OH:10])[C:27]([F:29])([F:28])[F:26])=[C:4]([Cl:25])[CH:3]=1

Participants

4

Reactant 3

HCID 67803Tetramethylammonium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 666973406-[2-(4-Bromo-2-chloro-phenyl)-propionyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 866458806-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

Procedure

In analogy to Example 1, step 3, 6-[2-(4-bromo-2-chloro-phenyl)-propionyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one was reacted with (trifluoromethyl)trimethylsilane and tetramethylammonium fluoride to give the title compound as a colorless solid. MS (m/e, ISP neg. ion)=496.0 [M−H+].

Sources & evidence

ORD record
ord-3616dadb55e94cc58cd582fc7d28bd58
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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