Chlorotrimethylsilane → 3,4-Dichlorophenethylamine

HRID 1843976Notes

Reaction equation

HRID 1843976 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[N+:10]([O-])=O)=[CH:4][C:3]=1[Cl:13].[Li+].[BH4-].Cl[Si](C)(C)C>C1COCC1>[Cl:13][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][NH2:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 53722591,2-Dichloro-4-[(E)-2-nitroethenyl]benzene

Product 1

HCID 2179583,4-DichlorophenethylamineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using an analogous procedure and workup as described for the preparation of intermediate I-15b, (E)-1,2-dichloro-4-(2-nitrovinyl)benzene (I-55a: 6.2 g, 28.97 mmol) in dry THF (62 mL) was reacted with LiBH4 (2.52 g, 115.887 mmol) and chlorotrimethylsilane (25.17 g, 231.768 mmol) at 0° C. The resulting mixture was stirred at room temperature for 40 hours to afford 5.3 g of the product (98% yield).

Sources & evidence

ORD record
ord-facaad2d037247c1b2d460ade0510a58
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…