Sodium sulfate decahydrate → (2-Chloro-4,5-difluorophenyl)methanol

HRID 253438Notes

Reaction equation

HRID 253438 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[CH:6][C:5]=1[Cl:12].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.[AlH4-].[Li+]>[Cl:12][C:5]1[CH:6]=[C:7]([F:11])[C:8]([F:10])=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

5

Reactant 2

HCID 62649Sodium sulfate decahydrateHCID 22149760Methyl 2-chloro-4,5-difluorobenzoate

Product 1

HCID 720763(2-Chloro-4,5-difluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 28112Lithium aluminum hydrideSolvent

Procedure

To 2-chloro-4,5-difluoro-benzoic acid methyl ester (119, 5.70 g, 0.0276 mol) in tetrahydrofuran (120.0 mL), 1.00 M of lithium tetrahydroaluminate in tetrahydrofuran (30.0 mL) was added slowly under an atmosphere of nitrogen. The reaction was stirred at room temperature for 4 hours, followed by adding sodium sulfate decahydrate. After 30 minutes, the reaction mixture was filtered, concentrated and purified with silica gel column chromatography eluting with 8% methanol in dichloromethane to give a white solid (120, 4.20 g, 85.2%).

Workup

  1. waitAfter 30 minutes
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 8% methanol in dichloromethane
  6. customto give a white solid (120, 4.20 g, 85.2%)

Sources & evidence

ORD record
ord-1a335e479b1048a48dc2c4850ced366c
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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