N-bromobutanimide → 4-Bromo-2,6-difluorophenol

HRID 1484322Notes

Reaction equation

HRID 1484322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[Br:10]N1C(=O)CCC1=O>CN(C=O)C>[Br:10][C:6]1[CH:7]=[C:2]([F:1])[C:3]([OH:9])=[C:4]([F:8])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 943922,6-Difluorophenol

Product 1

HCID 27362924-Bromo-2,6-difluorophenolYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-Difluorophenol (10.0 g, 76.86 mmoles) in DMF (60 mll), N-bromosuccinimide (13.68 g, 76.86 mmoles) was added at 0° C. and stirred at RT for 20 h. The reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as light yellow liquid (15.1 g, 93% yield). 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.49 (s, 1H), 7.35 (d, J=6.2 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fc1d75ae1c84948aff87cfc06a89106
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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