Acetic Acid → 1-(4-Bromothiophen-2-yl)-N,N-dimethylmethanamine

HRID 2281744Notes

Reaction equation

HRID 2281744 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[CH3:9][NH:10][CH3:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:10]([CH3:11])[CH3:9])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 877924-Bromothiophene-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 223495551-(4-Bromothiophen-2-yl)-N,N-dimethylmethanamineYield 77.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-bromothiophene-2-carbaldehyde (1.91 g, 10 mmol) and dimethylamine (2 M in THF, 7.5 mL, 15 mmol) in DCE (30 mL) was added NaBH(OAc)3 (2.65 g, 12.5 mmol), followed by AcOH (0.2 mL). After addition, the resulting mixture was stirred O/N at rt. The reaction was quenched with sat. NaHCO3 (20 mL) and brine, and was then extracted with EtOAc (100 mL+30 mL). The solvents were removed in vacuo to afford the crude title compound as a light yellow liquid (1.70 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.15 (s, 1H), 6.84 (s, 1H), 3.60 (s, 2H), 2.29 (s, 6H); MS ESI 219.7 [M+H]+, calcd for [C7H10BrNS+H]+ 220.0.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched with sat. NaHCO3 (20 mL) and brine
  3. extractionwas then extracted with EtOAc (100 mL+30 mL)
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-60dad3aaee994355b9233732eb83b201
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

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