Dimethylformamide → 4-Bromo-2,5-difluorobenzaldehyde

HRID 1924014Notes

Reaction equation

HRID 1924014 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].CN(C)[CH:13]=[O:14].[NH4+].[Cl-]>O1CCCC1>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([CH:13]=[O:14])=[C:3]([F:10])[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 675961,4-Dibromo-2,5-difluorobenzene

Product 1

HCID 224890814-Bromo-2,5-difluorobenzaldehydeYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To 1,4-dibromo-2,5-difluorobenzene (10.28 g, 37.81 mmol) in tetrahydrofuran (80 mL) at −40° C. was isopropylmagnesium chloride lithium chloride complex (29.1 mL, 37.81 mmol) added dropwise. After 1 h at −40° C. was N,N-dimethylformamide (58 mL, 756 mmol) added and the mixture was stirred for 30 minutes at −40° C. NH4Cl (2M, aq, 100 mL) was added and the mixture was extracted with ethyl acetate. The organic phase was dried with MgSO4 and concentrated to give 4-bromo-2,5-difluorobenzaldehyde (6.20 g, 74%) as a solid.

Workup

  1. customat −40° C.
  2. additionadded dropwise
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4e4092541b69455e932f50db8737cdd0
Source dataset
uspto-grants-2012_05
Patent number
US08178529B2

Reaction notes

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