Chlorotrimethylsilane → Benzeneethanamine, 3-fluoro-4-(trifluoromethyl)-

HRID 1843948Notes

Reaction equation

HRID 1843948 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:13]([F:16])([F:15])[F:14].Cl[Si](C)(C)C.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][C:3]=1[C:13]([F:15])([F:16])[F:14]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 1239141472-Fluoro-4-(2-nitro-vinyl)-1-trifluoromethyl-benzene

Product 1

HCID 57978173Benzeneethanamine, 3-fluoro-4-(trifluoromethyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-4-(2-nitro-vinyl)-1-trifluoromethyl-benzene (I-47a: 2.8 g, 11.914 mmol) was reacted with chlorotrimethylsilane (10.328 g, 95.07 mmol), LiBH4 (1.03 g 47.65 mmol) and THF (40 mL). The resulting mixture was stirred at room temperature for 72 hours to afford 2.46 g of the product (100% yield), LCMS: 99.49%, m/z=208.0 (M+1)

Sources & evidence

ORD record
ord-8d5d20e5f6d942d1b5ae89e072aff3a4
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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