Bis(4-cyanophenyl)methanol

4,4'-methanol-bisbenzonitrile is a diarylmethane.

4-[(4-Cyanophenyl)(hydroxy, )methylJbenzonitrile (lOu, Q1=CN, Q4=CN). To a solution ofiPrMgCl LiCl complex 1.3 M in THF (10.5 ml) at -15°C 4-bromobcnzonitrilc (1.4 g, 7.6 mmol) in THF (4 ml) was added dropwise over 15 mm. The brown solution was stirred for 30 mm at -15 °C and 1.5 h at it The solution was added dropwise to a yellowish solution of 4- formylbenzonitrile (1.0 g, 7.6 mmol) in THF (4 ml) over 10 mm at -15°C. After 1 h stirring at 0°C the light green solution was quenched with aq. sat. NH4C1 (20 ml), TBME (30 ml) andwater (20 ml) were added. After separation of the organic layer the inorganic phase was extracted with TBME (2 x 20 ml). The organic layers were washed with aq. sat. NaC1, combined, dried over Na2SO4 and concentrated at reduced pressure. To the liquid crude product (2 g) EtOAc/hept 1:2 was added. An insoluble pale yellow solid (0.54 g) was filtered off, dissolved in diethylether and precipitated with pentane to afford a pale yellow solid lOu(0.49 g, 27.5percent). The mother liquor was concentrated at reduced pressure and was purified by silica gel flash chromatography (EtOAc/hept 1:2) to afford a pale yellow solid lOu (0.23 g, 13percent).4-[(4-Cyanophenyl)carbonylJbenzonitrile (6u). A suspension of 4-[(4- cyanophenyl)(hydroxy)methyl]benzonitrile (lOu) (0.68 g, 2.9 mmol), CHC13 (25 ml) and Mn02 (1.7 g, 17.4 mmol) was stirred for 1 h at it. Mn02 (0.8 g, 8.7 mmol) was added again and the suspension was stirred for 1.5 h at it. The suspension was filtered and to the yellowsolution Mn02 (1.7 g, 17.4 mmol) was added and stirred for 2 h again. After a new addition of Mn02 (0.3 g, 2.9 mmol) and stirring for 1 h the starting material was totally consumed. The Mn02 was filtered off and the filtrate was concentrated at reduced pressure to afford a pale yellow solid 6u (0.57 g, 85percent).4-[(4-Cyanophenyl)(hydroxy, )methylJbenzonitrile (lOu, Q1=CN, Q4=CN). To a solution ofiPrMgCl LiCl complex 1.3 M in THF (10.5 ml) at -15°C 4-bromobcnzonitrilc (1.4 g, 7.6 mmol) in THF (4 ml) was added dropwise over 15 mm. The brown solution was stirred for 30 mm at -15 °C and 1.5 h at it The solution was added dropwise to a yellowish solution of 4- formylbenzonitrile (1.0 g, 7.6 mmol) in THF (4 ml) over 10 mm at -15°C. After 1 h stirring at 0°C the light green solution was quenched with aq. sat. NH4C1 (20 ml), TBME (30 ml) andwater (20 ml) were added. After separation of the organic layer the inorganic phase was extracted with TBME (2 x 20 ml). The organic layers were washed with aq. sat. NaC1, combined, dried over Na2SO4 and concentrated at reduced pressure. To the liquid crude product (2 g) EtOAc/hept 1:2 was added. An insoluble pale yellow solid (0.54 g) was filtered off, dissolved in diethylether and precipitated with pentane to afford a pale yellow solid lOu(0.49 g, 27.5percent). The mother liquor was concentrated at reduced pressure and was purified by silica gel flash chromatography (EtOAc/hept 1:2) to afford a pale yellow solid lOu (0.23 g, 13percent).

A metabolite of Letrozole

Molecular Weight:234.25
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:234.079312947
Monoisotopic Mass:234.079312947
Topological Polar Surface Area:67.8
Heavy Atom Count:18
Complexity:322
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes