Diisobutylaluminumhydride → (4-Bromo-3-fluorophenyl)methanol

HRID 1011655Notes

Reaction equation

HRID 1011655 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([F:11])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[F:11]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21951878Methyl 4-bromo-3-fluorobenzoate

Product 1

HCID 20682297(4-Bromo-3-fluorophenyl)methanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-3-fluoro-benzoic acid methyl ester (5.3 g, 22.9 mmol) in dry THF (60 mL) was added diisobutylaluminum hydride (30 mL) dropwise, This mixture was stirred overnight at room temperature until the starting material had been consumed, quenched with saturated aqueous potassium tartrate solution and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to give white solid product (4.3 g, 92%).

Workup

  1. customhad been consumed
  2. customquenched with saturated aqueous potassium tartrate solution
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b62dbe9ac0954e67850a7f4b437fa8ab
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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