Water → 5-Bromo-2-(difluoromethyl)benzonitrile

HRID 1255221Notes

Reaction equation

HRID 1255221 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([F:10])[F:9])=[C:4](F)[CH:3]=1.[C-:12]#[N:13].[K+].O.CCCCCC>CN1C(=O)CCC1.C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([F:10])[F:9])=[C:4]([CH:3]=1)[C:12]#[N:13]

Participants

8

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 9032Potassium CyanideHCID 27611824-Bromo-1-(difluoromethyl)-2-fluorobenzene

Product 1

HCID 671590075-Bromo-2-(difluoromethyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-bromo-1-(difluoromethyl)-2-fluorobenzene (5.0 g, 22 mmol) and KCN (4.34 g, 67 mmol) was heated at 150° C. in NMP (50 mL) for 16 h. After trituration with a mixture of water, hexane, EtOAc and DCM, the organic layer was concentrated and purified by silica gel flash chromatography using hexanes:DCM (4:1 to 4:1.5 v/v) as mobile phase to yield the title compound: 1H NMR (500 MHz, CD2Cl2) δ 7.97 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 6.95 (t, J=54.5 Hz, 1H).

Workup

  1. concentrationthe organic layer was concentrated
  2. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b8fcfff052d74ceb8dc472a91537d1f8
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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