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

HRID 1476188Notes

Reaction equation

HRID 1476188 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-d7b43212056d47d8aafa52f7a6e81fc1
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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