Water → 3-Bromo-6-chloro-2-fluorobenzaldehyde

HRID 2235184Notes

Reaction equation

HRID 2235184 reaction equation
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[F:17].CN([CH:21]=[O:22])C.O>C1COCC1>[Br:9][C:10]1[C:11]([F:17])=[C:12]([C:13]([Cl:16])=[CH:14][CH:15]=1)[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 1372751-Bromo-4-chloro-2-fluorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 592994573-Bromo-6-chloro-2-fluorobenzaldehydeYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a 2M LDA in THF (22 mL, 44 mmol) to 1-bromo-4-chloro-2-fluorobenzene (9.2 g, 44 mmol) in THF (100 mL) at −78° C. Stir for 10 minutes. Add DMF (10 mL, 132 mmol) and warm up to room temperature. Add the reaction mixture to ice and water. Extract the mixture with ethyl acetate (100 mL). Wash the organic layer with aqueous LiCl (20 mL, 10%), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to obtain 5 g (48%) of the title compound as a white solid.

Workup

  1. extractionExtract the mixture with ethyl acetate (100 mL)
  2. washWash the organic layer with aqueous LiCl (20 mL, 10%)
  3. dry with materialdry with magnesium sulfate
  4. filtrationfilter
  5. customevaporate solvent under reduced pressure

Sources & evidence

ORD record
ord-59aea86025c54e2395fd5495967126be
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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