Diethyl Ether → 4-Bromo-2,5-difluorobenzaldehyde

HRID 2179978Notes

Reaction equation

HRID 2179978 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([F:13])[C:10]([Br:14])=[CH:9][C:8]=1[F:15].[CH2:16]([O:18]CC)C>O>[Br:14][C:10]1[C:11]([F:13])=[CH:12][C:7]([CH:16]=[O:18])=[C:8]([F:15])[CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 224890814-Bromo-2,5-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (1.95M in hexanes, 10.2 ml)) was added dropwise to a stirred solution of 1,4-dibromo-2,5-difluorobenzene (5 g, 18.4 mmol) in diethyl ether (60 ml) at −70° C. After 1 h, the solution was warmed to 0° C. over 1 h, diluted with water, the layers separated and the ether layer dried over sodium sulphate and evaporated. Purification by column chromatography (Biotage), eluting with 5% ethyl acetate/hexane, gave a yellow oil (1.82 g).

Workup

  1. customthe layers separated
  2. dry with materialthe ether layer dried over sodium sulphate
  3. customevaporated
  4. customPurification by column chromatography (Biotage)
  5. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e673f6f778954398a4bcb09684223e9d
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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