Acetic Acid → HCID 12329868, compound

HRID 1988019Notes

Reaction equation

HRID 1988019 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[O:20][C:19]([CH:21]=O)=[CH:18][CH:17]=1.[CH3:23][NH:24][CH3:25].CC(O)=O>ClCCCl>[Br:15][C:16]1[O:20][C:19]([CH2:21][N:24]([CH3:25])[CH3:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 6003285-Bromofuran-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12329868HCID 12329868, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (844 mg, 4 mmol) was added to a solution of 5-bromo-furan-2-carbaldehyde (350 mg, 2 mmol) and dimethyl amine (2 ml, 2M solution in THF) in 10 ml of 1,2-dichloroethane (DCE). 0.2 ml of HOAc was then added. The mixture was stirred at room temperature overnight, followed by addition of 15 ml of DCE. The organic phase was washed with water, dried over sodium sulfate. The solvent was removed by rotovap to give 400 mg of (5-bromo-furan-2-ylmethyl)-dimethyl-amine, yield: 97%.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-fd33237004d044cc96a86ec0314c1598
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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