Methyl 3-(bromomethyl)-2-benzofurancarboxylate → Methyl 3-dimethylaminomethylbenzofuran-2-carboxylate

HRID 914261Notes

Reaction equation

HRID 914261 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH2:10]Br)=[O:4].[CH3:16][NH:17][CH3:18].C1COCC1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH2:10][N:17]([CH3:18])[CH3:16])=[O:4]

Participants

5

Reactant 2

HCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylateHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 59710963Methyl 3-dimethylaminomethylbenzofuran-2-carboxylateYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromomethylbenzofuran-2-carboxylic acid methyl ester (269 mg, 1 mmol) was dissolved in anhydrous DMF and added 2M dimethylamine/THF solution (1.5 ml, 3 mmol). After 1-2 h, the reaction was diluted with EtOAc and washed twice with saturated NaHCO3 (aq.) and brine. The organic extract over was dried over Na2SO4 and then concentrated in vacuo. The crude was purified on a silica gel column (5% MeOH in dichloromethane) to give 3-dimethylaminomethylbenzofuran-2-carboxylic acid methyl ester (131 mg).

Workup

  1. washwashed twice with saturated NaHCO3 (aq.) and brine
  2. extractionThe organic extract
  3. dry with materialover was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified on a silica gel column (5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a94fb4e1a67849fa93c242eadfb1f472
Source dataset
uspto-grants-2011_09
Patent number
US08026371B2

Reaction notes

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