N-bromobutanimide → 1-Bromo-2-[bromo(difluoro)methyl]benzene

HRID 1255225Notes

Reaction equation

HRID 1255225 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([F:10])[F:9].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([Br:11])([F:10])[F:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27611811-Bromo-2-(difluoromethyl)benzene

Product 1

HCID 671595551-Bromo-2-[bromo(difluoro)methyl]benzene

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-bromo-2-difluoromethylbenzene (9.6 g, 46.8 mmol) and N-bromosuccinimide (24.8 g, 139 mmol) in carbon tetrachloride (100 mL) was irradiated with a sunlamp. After 3 days, the reaction mixture was diluted with hexane, the precipitate was filtered off, and the collected organic filtrate was concentrated in vacuo. Purification by flash chromatography on silica gel (100% hexanes) provided the title compound: 1H NMR (500 M=Hz, CD2Cl2) δ7.74 (d, J=8.0 Hz, 1H), 7.66 (dd, J=8.0, 1.5 Hz, 1H), 7.44 (t, J=7.7 Hz, 1H), 7.37 (td, J=7.7, 1.3 Hz, 1H).

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationthe collected organic filtrate was concentrated in vacuo
  3. customPurification by flash chromatography on silica gel (100% hexanes)

Sources & evidence

ORD record
ord-72a4a7eac7b1429c8db2166312285396
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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