Dimethylformamide → 4-Bromo-2,6-difluorobenzaldehyde

HRID 1819497Notes

Reaction equation

HRID 1819497 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:15]=[C:16]([Br:21])[CH:17]=[C:18]([F:20])[CH:19]=1.[Cl-].[NH4+].CN([CH:27]=[O:28])C>C1COCC1.CCCCCC>[Br:21][C:16]1[CH:15]=[C:14]([F:13])[C:19]([CH:27]=[O:28])=[C:18]([F:20])[CH:17]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 27732904-Bromo-2,6-difluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a THF (250 mL) solution of diisopropylamine (53 mL) was added 2.44 M hexane solution of butyl lithium at −78° C., and the reaction mixture was stirred for 30 miniute. To the reaction mixture was added a THF solution of 3,5-difluorobromobenzene (1) (36 g), and then the reaction mixture was stirred for 1 h. To the reaction mixture was added DMF 146 mL, and the reaction mixture was stirred for additional 1 h. To the reaction mixture was added a saturated ammonium chloride aqueous solution, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=20:1) to obtain the compoumd (2) 23.2 g.

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. stirringthe reaction mixture was stirred for additional 1 h
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-fd3f069efc494c0f825e9a149babd938
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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