N-bromobutanimide → 5-Bromo-3-fluoro-2-hydroxybenzaldehyde

HRID 1296210Notes

Reaction equation

HRID 1296210 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Br:11]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[Br:11][C:8]1[CH:9]=[C:2]([F:1])[C:3]([OH:10])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 27792765-Bromo-3-fluoro-2-hydroxybenzaldehydeYield 99.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

596 mg of 3-fluoro-2-hydroxybenzaldehyde was dissolved in 5 ml of acetonitrile, and 770 mg of N-bromosuccinimide was added. The solution was stirred for 15 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent was evaporated, to give 928 mg of 5-bromo-3-fluoro-2-hydroxybenzaldehyde.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe solution was filtered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ce3a698aac8640afbe3048ef15a0ed5c
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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