1,5-Dibromopentane → 1-(3-FLUOROPHENYL)CYCLOHEXANECARBONITRILE

HRID 333267Notes

Reaction equation

HRID 333267 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 81001,5-DibromopentaneHCID 68145Benzeneacetonitrile, 3-fluoro-

Product 1

HCID 7361251-(3-FLUOROPHENYL)CYCLOHEXANECARBONITRILEYield 98.2%

Procedure

The title compound was prepared from 2-(3-fluorophenyl)acetonitrile (2.58 ml, 22.2 mmol) and 1,5-dibromopentane (3.324 ml, 24.4 mmol) according to General Procedure J to yield 1-(3-fluorophenyl)cyclohexanecarbonitrile (4.43 g, 97%) as a clear oil. 1H NMR (CDCl3) δ 1.26-1.39 (m, 1H), 1.76-1.88 (m, 7H), 2.17 (d, J=11.2 Hz, 2H), 6.93-6.98 (m, 1H), 7.04 (d, J=8.0 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 7.30-7.35 (m, 1H). 13C NMR (CDCl3) δ 23.7, 25.0, 37.5, 44.6, 122.5, 125.0, 125.1, 126.0, 129.5, 130.0, 142.8.

Sources & evidence

ORD record
ord-b32a57f23d814c8282da8a07f7b7105f
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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