Dimethylformamide → 6-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde

HRID 1782612Notes

Reaction equation

HRID 1782612 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[C:4]([F:13])[CH:3]=1.CC1CCCN(C)C1(C)C.[Li].CN([CH:28]=[O:29])C>C1COCC1>[Cl:1][C:2]1[C:3]([CH:28]=[O:29])=[C:4]([F:13])[C:5]([Si:9]([CH3:10])([CH3:12])[CH3:11])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 18935733(4-Chloro-2,6-difluorophenyl)trimethylsilaneHCID 66701855Lithium tetramethylpiperidine

Product 1

HCID 866138416-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehydeYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-chloro-3,5-difluoro-4-trimethylsilylbenzene (1.5 g, 6.8 mmol) in THF (10 mL) was added to a solution of lithium tetramethylpiperidine (14 mmol) in THF (15 mL) at −75° C. The solution was stirred for 2 hours then DMF (1.5 g, 20 mmol) was added and the solution allowed to warm to ambient temperature. The reaction was quenched with a saturated solution of ammonium chloride (25 mL) and extracted with ethyl ether (2×25 mL) and the combined extracts dried (sodium sulfate) and concentrated. The residue was purified by chromatography (hexanes) to give 6-chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde (1.4 g, 5.6 mmol): LC/MS (m/z=248).

Workup

  1. customThe reaction was quenched with a saturated solution of ammonium chloride (25 mL)
  2. extractionextracted with ethyl ether (2×25 mL)
  3. dry with materialthe combined extracts dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (hexanes)

Sources & evidence

ORD record
ord-a53d013cd6db4dce9d7e555bc1afee8a
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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