N-bromobutanimide → HCID 59494875, compound

HRID 872019Notes

Reaction equation

HRID 872019 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:20]2[CH2:21][CH2:22][O:23][C:19]=2[CH:18]=[C:17]([CH2:24][OH:25])[CH:16]=1>ClCCl>[Br:1][C:16]1[C:17]([CH2:24][OH:25])=[CH:18][C:19]2[O:23][CH2:22][CH2:21][C:20]=2[C:15]=1[O:14][CH2:13][CH2:12][CH2:11][O:10][CH3:9].[Br:1][C:18]1[C:19]2[O:23][CH2:22][CH2:21][C:20]=2[C:15]([O:14][CH2:13][CH2:12][CH2:11][O:10][CH3:9])=[CH:16][C:17]=1[CH2:24][OH:25]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59494791HCID 59494791, compound

Product 2

HCID 59494875HCID 59494875, compoundHCID 59494942HCID 59494942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (1.04 g) was added to a solution of [4-(3-methoxypropoxy)-2,3-dihydro-1-benzofuran-6-yl]methanol (1.27 g) in dichloromethane (25 ml) under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was concentrated in vacuo and the resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/2) to give [5-bromo-4-(3-methoxypropoxy)-2,3-dihydro-1-benzofuran-6-yl]methanol (860 mg) and [7-bromo-4-(3-methoxypropoxy)-2,3-dihydro-1-benzofuran-6-yl]methanol (540 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-4929c88baead4c40a9778f7f480bb54d
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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