1,3-Dibromopropane → HCID 11303095, compound

HRID 843124Notes

Reaction equation

HRID 843124 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:9]=2[C:10]=1[CH:11]1[CH2:13][CH2:12]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27][CH2:28]Br>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:28][CH2:27][CH2:26][Br:25])[C:9]=2[C:10]=1[CH:11]1[CH2:12][CH2:13]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 54530068HCID 54530068, compound

Product 1

HCID 11303095HCID 11303095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-cyclopropyl-4-hydroxy-benzofuran-2-carboxylic acid ethyl ester (92 mg) and potassium carbonate (62 mg) in N,N-dimethylformamide (1.5 ml) was added 1,3-dibromopropane (190 μl) and the reaction mixture was stirred for 2 hours at room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution (5 ml) and diluted with ethyl acetate (8 ml). The organic layer was washed with water (5 ml twice) and brine, dried over anhydrous sodium sulfate, then concentrated in vacuo to dryness. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate to give 4-(3-bromo-propoxy)-3-cyclopropyl-benzofuran-2-carboxylic acid ethyl ester (120 mg) as a white solid. EI-MS: m/z 368 (M+); 1H-NMR (CDCl3): δ 0.91-0.95 (4H, m), 1.37 (3H, t, J=7.26 Hz), 2.36 (2H, quintet, J=7.26 Hz), 2.47-2.51 (1H, m), 3.60 (2H, t, J=7.26 Hz), 4.16 (2H, t, J=7.26 Hz), 4.37 (2H, q, J=7.26 Hz), 6.58 (1H, d, J=8.25 Hz), 7.07 (1H, d, J=8.25 Hz), 7.24 (1H, dd, J=8.25 Hz, 8.25 Hz).

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (5 ml)
  2. additiondiluted with ethyl acetate (8 ml)
  3. washThe organic layer was washed with water (5 ml twice) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fbddd79c63d44895874a2deb7f19fb78
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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