Triphenylphosphine → trans-2-Bromomethyl-N-cyanomethylcyclohexanecarboxamide

trans-N-Cyanomethyl-2-hydroxymethyl-cyclohexanecarboxamide (12.4 g, 63.2 mmol) and triphenylphosphine (19.9 g, 75.8 mmol) were weighed into a 1000 mL round bottom flask fitted with a stir bar, addition port and nitrogen inlet. A nitrogen atmosphere was established and maintained and then anhydrous tetrahydrofuran (300 mL) was added. The reaction mixture was stirred for 30 minutes at room temperature and N-bromosuccinimide (13.5 g, 75.8 mmol) was added to the flask. The reaction slowly cleared to an orange-red solution. The reaction mixture was stirred at room temperature for 18 h and then concentrated on a rotary evaporator. Product was purified from the residue by chromatography on 2360 cm3 of silica gel in a 10×30 cm column with ethyl acetate eluent. The product fractions were concentrated on a rotary evaporator and the residue dried under high vacuum to give trans-2-bromomethyl-N-cyanomethylcyclo-hexanecarboxamide as a white solid with a slight yellow tint.

1. customfitted with a stir bar
2. additionaddition port and nitrogen inlet
3. temperaturemaintained
4. customThe reaction
5. stirringThe reaction mixture was stirred at room temperature for 18 h
6. concentrationconcentrated on a rotary evaporator
7. customProduct was purified from the residue by chromatography on 2360 cm3 of silica gel in a 10×30 cm column with ethyl acetate eluent
8. concentrationThe product fractions were concentrated on a rotary evaporator
9. customthe residue dried under high vacuum

ORD record

ord-53148dd092a6484e9997f7f06110366c

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07371747B2