4-Oxo-1-phenylcyclohexanenitrile → 4-(5-Fluoropyridin-2-yl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

HRID 657508Notes

Reaction equation

HRID 657508 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[O:9]=[C:10]1[CH2:15][CH2:14][C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:16]#[N:17])[CH2:12][CH2:11]1>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2([OH:9])[CH2:15][CH2:14][C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:16]#[N:17])[CH2:12][CH2:11]2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 594425454-(5-Fluoropyridin-2-yl)-4-hydroxy-1-phenylcyclohexanecarbonitrileYield 89.1%

Procedure

According to the process described in Example 260, 25 mmol of 2-bromo-5-fluoropyridine were converted into the Grignard reagent and reacted with 25 mmol of 4-oxo-1-phenylcyclohexanecarbonitrile (dissolved in 100 ml of THF). The chromatographic separation of the crude product (silica gel flash column; HEP/EA 3:1) afforded two main fractions (TLC (HEP/EA 1:1): Rf 0.58 and 0.49), which were combined. 6.6 g of the title compound (cis/trans mixture) were obtained as a viscous yellow oil.

Workup

  1. customThe chromatographic separation of the crude product (silica gel flash column; HEP/EA 3:1)
  2. customafforded two main fractions (TLC (HEP/EA 1:1): Rf 0.58 and 0.49), which

Sources & evidence

ORD record
ord-d2144595d79b48bc87bd715d0e563205
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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