Bromotrichloromethane → 5-Bromo-2-[bromo(difluoro)methyl]benzonitrile

HRID 1255222Notes

Reaction equation

HRID 1255222 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]([F:12])[F:11])=[C:6]([CH:9]=1)[C:7]#[N:8].C([Br:17])(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([Br:17])([F:11])[F:12])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 3

HCID 6383BromotrichloromethaneHCID 10340Sodium CarbonateHCID 671590075-Bromo-2-(difluoromethyl)benzonitrile

Product 1

HCID 671591025-Bromo-2-[bromo(difluoro)methyl]benzonitrile

Procedure

A mixture of the title compound from Example 302 Step A (2.44 g, 10.5 mmol), CCl3Br (8 mL) and Na2CO3 (480 mg, 4.5 mmol) in a sealed vessel was illuminated by a sunlamp for 30 h. Purification by silica gel flash chromatography using 8:1 to 6:1 to 4:1 hexanes:DCM as mobile phase yielded the title compound: 1H NMR (500 MHz, CD2Cl2) δ 8.03 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H).

Workup

  1. customwas illuminated by a sunlamp for 30 h
  2. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-78cc48c27a9340cfbd0a72da2252fa6b
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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