1-Bromo-2,6-difluorobenzene → HCID 22473553, compound

HRID 2183971Notes

Reaction equation

HRID 2183971 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[F:9].CC1(C)C(C)(C)OB([C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])O1>>[CH3:24][CH2:25][CH2:18][CH:19]([CH3:22])[CH3:20].[F:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[C:18]1[C:19]([C:20]#[N:21])=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 1235571-Bromo-2,6-difluorobenzeneHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 2

HCID 78922-MethylpentaneHCID 22473553HCID 22473553, compoundYield 153.7%

Procedure

2-Bromo-1,3-difluorobenzene (3.0 g, 15.5 mmol) was coupled to 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (4.63 g, 20.2 mmol) as described in Example 51. The resulting black solid was purified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (10-15%). Trituration with isohexane (20 ml) gave 2′,6′-difluorobiphenyl-2-carbonitrile as a pale yellow solid (3.34 g, 100%): δH (360 MHz, CDCl3) 7.06 (2H, dd, J 8 and 7), 7.38-7.44 (1H, m), 7.47-7.56 (2H, m), 7.61-7.72 (1H, m), 7.82 (1H, dd, J 8 and 1).

Workup

  1. customThe resulting black solid was purified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (10-15%)

Sources & evidence

ORD record
ord-078415246be74e718f64ce6e9cd64adc
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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