Hydrochloric Acid → 3-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde

HRID 1418482Notes

Reaction equation

HRID 1418482 reaction equation
[Li]C(CC)C.[Si:6]([O:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].CN([CH:25]=[O:26])C.Cl>C1COCC1>[Si:6]([O:13][C:14]1[C:15]([F:21])=[C:16]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH:25]=[O:26])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11230299tert-Butyl(2,5-difluorophenoxy)dimethylsilaneHCID 178418400CID 53628100

Product 1

HCID 113463223-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehydeYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0M solution of sec-BuLi (21.5 ml, 21.5 mmol) was added dropwise to a stirred solution of O-tert-butyldimethylsilyl-2,5-difluorophenol (5.0 g, 20 mmol) in THF (20 mL) at -78° C. After 0.5 hr DMF (1.9 ml, 24.6 mmol) was added dropwise while the temperature was kept below -70° C. After 30 min, the mixture was allowed to warm to room temperature over 30 min. To the mixture was added 3N HCl (30 ml) and stirring was continued for 30 min. The mixture was extracted with ether (100 ml) and the extract was washed with water (100 ml), brine (100 ml), dried (sodium sulfate) and evaporated. Column chromatography (silica gel) of the residue eluting with n-hexane gave 3.56 g (64%) of the titled compound as a colorless oil.

Workup

  1. customwas kept below -70° C
  2. waitwas continued for 30 min
  3. extractionThe mixture was extracted with ether (100 ml)
  4. washthe extract was washed with water (100 ml), brine (100 ml)
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. washColumn chromatography (silica gel) of the residue eluting with n-hexane

Sources & evidence

ORD record
ord-25f96532e94945e0a6de5dea53d61c04
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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