Boron tribromide → 1-(Hydroxymethyl)-3-methylenecyclobutane-1-carbonitrile
Reaction equation
C[O:2][CH2:3][C:4]1([C:9]#[N:10])[CH2:7][C:6](=[CH2:8])[CH2:5]1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][CH2:3][C:4]1([C:9]#[N:10])[CH2:7][C:6](=[CH2:8])[CH2:5]1Participants
4
Procedure
To a mixture of 1-(methoxymethyl)-3-methylenecyclobutanecarbonitrile (1.40 g, 0.0102 mol) in methylene chloride (30 mL, 0.4 mol) was added 1.0 M of boron tribromide in methylene chloride (12.8 mL) at −78° C. The reaction was stirred at rt for 2 h, quenched with aq. sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated to dryness to give the desired product (1.26 g, 100%). 1H NMR (400 MHz, CDCl3): 4.81 (2H, m), 3.66 (2H, s), 3.10 (2H, m), 2.59 (2H, m) ppm.
Workup
- customquenched with aq. sodium bicarbonate
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-14e47be5330f4388a53979b9a2dabac6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420629B2
Reaction notes
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