Diisobutylaluminum hydride → (4-Bromo-3,5-dichlorophenyl)methanol

HRID 1502791Notes

Reaction equation

HRID 1502791 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[C:20]([Cl:21])=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][C:12]=1[Cl:22]>C1COCC1>[Br:10][C:11]1[C:20]([Cl:21])=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[Cl:22]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 508496864-Bromo-3,5-dichloro-benzoic acid methyl ester

Product 1

HCID 54366784(4-Bromo-3,5-dichlorophenyl)methanolYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1M in toluene, 66 mL, and 66.0 mmol) was added dropwise to a stirred solution of methyl 4-bromo-3,5-dichlorobenzoate (7.5 g, 26.0 mmol) in THF (50 mL) at −78° C. The reaction mixture was allowed to warm toward ambient temperature and stirred for 6 h. The reaction mixture was poured into ice-water and extracted with CH2Cl2. The organic layer was washed with brine followed by water, dried (Na2SO4), filtered and concentrated to afford 6.0 g of a mixture of (4-bromo-3,5-dichlorophenyl)methanol and 4-bromo-3,5-dichlorobenzaldehyde—as an off white solid which was taken to next step without purification.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f85e238172f4056bbc472a3aa65edbe
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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