Chlorotrimethylsilane → 2-(3,4-Difluorophenyl)ethanamine

HRID 1843954Notes

Reaction equation

HRID 1843954 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[N+:10]([O-])=O)=[CH:4][C:3]=1[F:13].[Li+].[BH4-].Cl[Si](C)(C)C>C1COCC1>[F:13][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][NH2:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 247212971,2-difluoro-4-[(E)-2-nitroethenyl]benzene

Product 1

HCID 34669162-(3,4-Difluorophenyl)ethanamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using an analogous procedure and workup as described in for the preparation of intermediate I-15b above. (E-1,2-difluoro-4-(2-nitrovinyl)benzene (I-49a: 5 g, 27.027 mmol) in dry THF (81 mL) as reacted with LiBH4 (2.35 g, 108.1081 mmol) and chloro trimethyl silane (27.63 ml, 216.216 mmol) at 0° C. The resulting mixture was stirred at room temperature for 3 days to afford 4.2 g of the product (100% yield).

Workup

  1. customworkup as described in for the preparation of intermediate I-15b above

Sources & evidence

ORD record
ord-d08a19f1e27943218ead93e35550ed25
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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