1-Bromo-3-chloropropane → HCID 58755248, compound
Reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:20][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1Participants
5
Procedure
Methyl (6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate (2.71 g, 13.0 mmol) and 1-bromo-3-chloropropane (2.46 g, 15.6 mmol) were dissolved in N,N-dimethylformamide (15 mL), and potassium carbonate (1.98 g, 14.3 mmol) was added, and the mixture was stirred under nitrogen atmosphere at room temperature for 24 hr. The reaction mixture was concentrated under reduced pressure, and water added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) to give the title compound (2.95 g, yield 80%) as a colorless oil.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure, and water
- additionadded
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ddfe34107282471db80a5f2b71e7c01b
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820837B2
Reaction notes
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