Sodium Thiosulfate → (4-Bromo-3-fluorophenyl)methanol

HRID 2390112Notes

Reaction equation

HRID 2390112 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][C:9]=1[F:18].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1.CCOCC>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[F:18]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 21226445Aluminium lithium hydrideHCID 21951878Methyl 4-bromo-3-fluorobenzoate

Product 1

HCID 20682297(4-Bromo-3-fluorophenyl)methanolYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) suspension of lithium aluminium hydride (88 mg; 2.3 mmol) in anhydrous THF (10 mL) was treated dropwise with a solution of methyl 4-bromo-3-fluorobenzoate (Combi-Blocks; 300 mg; 1.29 mmol) dissolved in anhydrous Et2O (10 mL), and the reaction mixture was stirred at RT for 2 days. The reaction mixture was treated with a saturated aqueous solution of sodium thiosulfate. The organic phase was separated, dried over MgSO4, filtered and concentrated to dryness affording the title compound as a yellow liquid (247 mg, 94%).

Workup

  1. temperatureA cooled
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ae012942e9b44d5eb57467a5e527f735
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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