Pyridine → 4-(3-Methoxypropyl)-3-methyl-2-bromomethyl-1-benzofuran
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:17])=[C:13]([CH2:15]O)[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1.P(Br)(Br)[Br:25]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:17])=[C:13]([CH2:15][Br:25])[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1Participants
Procedure
To a solution of [4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanol (181 mg, 0.774 mmol) in dichloromethane (4 mL) at 0° C. was added pyridine (0.1 mL) followed by phosphorous tribromide (0.109 mL, 1.16 mmol). The cooling bath was removed and the solution was stirred for 1 hour at room temperature. After recooling to 0° C. the reaction was quenched by the addition of ice chips. The mixture was extracted with ethyl acetate and the combined organic layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium bromide. The solution was dried over sodium sulfate, filtered and reduced to dryness to furnish 188 mg (82%) of the [4-(3-methoxypropyl)-3-methyl-2-bromomethyl-1-benzofuran, which was directly carried on to the next step.
Workup
- customThe cooling bath was removed
- customAfter recooling to 0° C.
- customwas quenched by the addition of ice chips
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium bromide
- dry with materialThe solution was dried over sodium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-5c088cfae02e4e8e96442c5a91c55361
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420001B2
Reaction notes
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