Chlorotrimethylsilane → 2-(4-Bromothiophen-2-yl)ethan-1-amine

HRID 1843859Notes

Reaction equation

HRID 1843859 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N+:9]([O-])=O)[S:5][CH:6]=1.[Li+].[BH4-].Cl[Si](C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][CH2:8][NH2:9])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 27323634-bromo-2-(2-nitrovinyl)thiopheneHCID 4148881Lithium borohydride

Product 1

HCID 150366152-(4-Bromothiophen-2-yl)ethan-1-amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction conditions and workup as described in Example 14, step 2, 4-bromo-2-(2-nitro-vinyl)-thiophene (5 g, 21.367 mmol) in dry THF (150 mL) was reacted with LiBH4 (1.86 g, 85.470 mmol), chloro trimethyl silane (21.6 mL, 170.576 mmol) to afford 4.4 g of the crude product which was used in the next step without further purification.

Workup

  1. customreaction conditions and workup

Sources & evidence

ORD record
ord-b8e417b0f9044c2d84edc9f29bfb0afe
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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