Methanol → 2-(5-Bromothiophen-2-yl)ethan-1-amine

HRID 1843855Notes

Reaction equation

HRID 1843855 reaction equation
Cl[Si](C)(C)C.[Li+].[BH4-].[Br:8][C:9]1[S:10][C:11]([CH:14]=[CH:15][N+:16]([O-])=O)=[CH:12][CH:13]=1.CO>C1COCC1.C(Cl)(Cl)Cl>[Br:8][C:9]1[S:10][C:11]([CH2:14][CH2:15][NH2:16])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 543993982-Bromo-5-(2-nitro-vinyl)-thiophene

Product 1

HCID 49619472-(5-Bromothiophen-2-yl)ethan-1-amineYield 234.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dry THF (30 mL) and chloro trimethyl silane (12.42 mL, 98.24 mmol) were added dropwise to LiBH4 (1.128 g, 51.28 mmol) over a period of 10 minutes under nitrogen atmosphere. This was followed by dropwise addition of 2-bromo-5-(2-nitro-vinyl)-thiophene (I-14a: 3 g, 12.82 mmol) in dry THF (30 mL) over a period of 20 minutes and the resulting mixture was stirred at room temperature for 48 hours. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mixture was quenched with methanol and concentrated to afford 6.2 g of the crude product which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0f44291665c54adba1fdd46158e4c0fb
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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