3-(HYDROXYMETHYL)-5-(TRIFLUOROMETHYL)BENZONITRILE synthesis
- Product Name:3-(HYDROXYMETHYL)-5-(TRIFLUOROMETHYL)BENZONITRILE
- CAS Number:569370-38-3
- Molecular formula:C9H6F3NO
- Molecular Weight:201.15
Yield:569370-38-3 61%
Reaction Conditions:
tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 160; for 0.333333 h;Microwave irradition;
Steps:
45.A STEP A:
STEP A: Preparation of 3-hydroxymethyl-5-trifluoromethyl-benzonitrile A mixture of (3-bromo-5-trifluoromethyl-phenyl)-methanol (500 mg, 1.96 mmol), zinc cyanide (230 mg, 1.96 mmol) and tetrakis(triphenylphosphine) palladium (68 mg, 0.059 mmol) in DMF (2 ml) was heated by microwave at 160° C. for 20 minutes. The mixture was partitioned between ethyl ether (20 ml) and water (10 ml). The aqueous layer was extracted with ether and combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The product was purified on Biotage column (12+M), eluding with 2% ethyl acetate in heptane (1 CV), 2-20% (10 CV), 20% (2CV) to yield the title compound (240 mg, 61%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.05 (s, 1H) 4.8 (s, 2H) 7.82 (s, 1H) 7.86 (s, 2H).
References:
US2007/213371,2007,A1 Location in patent:Page/Page column 71
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