3,5-DIFLUORO-4-HYDROXY-BENZONITRILE

To a solution of aldoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol percent, 50percent soln in EtOAc) and the resulting reaction mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 .x. 20 mL) and the combined organic phase was washed with saturated NaHCO(iv) 3, 5-Difluoro-4-hydroxybenzonitrileBBrA mixture of ethyl 3-(bromomethyl)-4-fluorobenzo[b]thiophene-2-carboxylate I3 (25 mg, 0.079 mmol), A mixture of ethyl 3-(bromomethyl)-4-chlorobenzo[b]thiophene-2-carboxylate I5 (0.025 g, 0.075 mmol), General procedure: A mixture of the chloride 4 (1.0 eq), the appropriate alcohol (1.0 eq), and K2CCh or Cs2C03 (2.0 eq) in acetonitrile or A, A- d i m c t h y 1 fo r m a m i d c was stirred for a time period between 2h and overnight at a temperature ranging between room temperature and the reflux temperature. After cooling to rt, H20 was added and the reaction mixture was extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over Na2S04, filtered and evaporated under vacuum. The desired product was obtained after purification of the crude material as reported in the specific examples.[0352] To 2, 6-Difluoro-4-cyanophenol (2.5 g, 16.12 mmol, 1 equivalent) was added BH3- THF ( 1 M, 64.48 mL, 4 equivalent). The mixtiue was stirred at 70 C for 10 hours. The reaction was quenched by addition of HQ (6 M, 5 mL) at 25 C then it was concentrated under reduced pressure to give 38.1 (7.1 g, crude) as a white solid.

Molecular Weight:155.10
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:155.01827004
Monoisotopic Mass:155.01827004
Topological Polar Surface Area:44
Heavy Atom Count:11
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes