Dimethylformamide → 5-Bromo-2,4-difluorobenzaldehyde

HRID 2060775Notes

Reaction equation

HRID 2060775 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[C:17]([Br:19])[C:16]([F:20])=[CH:15][C:14]=1[F:21].CN(C)[CH:24]=[O:25]>C(OCC)C>[Br:19][C:17]1[C:16]([F:20])=[CH:15][C:14]([F:21])=[C:13]([CH:18]=1)[CH:24]=[O:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 105645111,5-Dibromo-2,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 222607695-Bromo-2,4-difluorobenzaldehydeYield 61.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.6 M solution of butyl lithium in hexane (114 mL, 182 mmol) is added to a −78° C. solution of 1,5-dibromo-2,4-difluorobenzene (41.3 g, 152 mmol) in diethyl ether (290 mL). Dimethylformamide (14.4 g, 198 mmol) is added and the reaction is stirred at −78° C. for 15 minutes. The reaction is quenched with 1 N HCl (300 mL), is diluted with water, and extracted three times with ethyl acetate. The organic layer is dried over sodium sulfate and the solvent is removed under reduced pressure to give crude material that is purified by silica gel chromatography with a linear gradient of 0% to 50% CH2Cl2 in hexanes over 30 minutes to give the title compound (20.51 g, 61%). GC-MS m/e (79Br/81Br) 220, 222.

Workup

  1. customThe reaction is quenched with 1 N HCl (300 mL)
  2. additionis diluted with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customto give crude material that
  7. customis purified by silica gel chromatography with a linear gradient of 0% to 50% CH2Cl2 in hexanes over 30 minutes

Sources & evidence

ORD record
ord-afb4c340752d4c5494ed407b2abf097f
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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