Dichloromethane → Methyl 2-(6-methoxy-1-benzofuran-3-yl)acetate
Reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.Cl[CH2:21]Cl>>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11]([O:13][CH3:21])=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(6-methoxybenzofuran-3-yl)acetic acid (0.6 g, 2.9 mmol) in anhydrous dichloromethane (20 mL) at −78° C. was added boron tribromide (1.5 eq.) The reaction was stirred at −78° C. for 30 minutes, 0° C. for 2 hours, and at room temperature overnight. The reaction mixture was cooled to 0° C. and quenched slowly with methanol. After stirring for 15 minutes a saturated sodium bicarbonate solution was added slowly to the mixture and allowed to stir at 0° C. for 30 minutes. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give methyl 2-(6-methoxybenzofuran-3-yl)acetate (745) (67%).
Workup
- customat room temperature
- customovernight
- temperatureThe reaction mixture was cooled to 0° C.
- customquenched slowly with methanol
- stirringAfter stirring for 15 minutes a saturated sodium bicarbonate solution
- additionwas added slowly to the mixture
- stirringto stir at 0° C. for 30 minutes
- additionEthyl acetate was added
- customthe layers were separated
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-89e2b2c218c640b983eae893b0cefcc3
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476308B2
Reaction notes
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