Chlorotrimethylsilane → 3,4-Dichlorophenethylamine

HRID 1843927Notes

Reaction equation

HRID 1843927 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 23629018984-16-2HCID 4148881Lithium borohydride

Product 1

HCID 2179583,4-DichlorophenethylamineYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using an analogous procedure and workup as described in Example 15, 1,2-dichloro-4-(2-nitro-vinyl)-benzene (I-41a: 5.1 g, 23.831 mmol) in dry THF (51 mL) was reacted with LiBH4 (2.1 g, 95.327 mmol) and chloro trimethyl silane (20.71 g, 190.64 mmol) at 0° C. The resulting mixture was stirred at room temperature for 72 hours to afford 3.43 g of the crude product which was used in the next step without further purification.

Sources & evidence

ORD record
ord-3a99f35ad7f64755a49fc4a4d67605fa
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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