Boron tribromide → 1-(Hydroxymethyl)-3-methylenecyclobutanecarbonitrile

HRID 1966149Notes

Reaction equation

HRID 1966149 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]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 668243071-(Methoxymethyl)-3-methylidenecyclobutane-1-carbonitrile

Product 1

HCID 668243411-(Hydroxymethyl)-3-methylenecyclobutanecarbonitrileYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. customquenched with aq. sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-14e47be5330f4388a53979b9a2dabac6
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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