Diisobutylaluminum hydride → (4-Bromo-3-methylphenyl)methanol

HRID 898196Notes

Reaction equation

HRID 898196 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][C:12]=1[CH3:21]>C(Cl)Cl>[Br:10][C:11]1[CH:20]=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[CH3:21]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIBALH (1.0M solution in methylene chloride, 31 mL, 31 mmol) was added dropwise to a solution of methyl 4-bromo-3-methylbenzoate (3.0 g, 14.0 mmol) in methylene chloride (20 mL) at 0° C. After 1 h, the reaction was quenched with 10% aqueous sodium bisulfite (100 mL). The aqueous layer was separated and extracted with methylene chloride (50 mL). The combined organic layers were combined, dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 17% ethyl acetate/hexane gave 1.90 g (9.50 mmol, 68%) of product: 1H NMR (500 MHz) δ 7.50 (d, J=8.3 Hz, 1H), 7.24 (s, 1H), 7.04 (d, J=8.0 Hz, 1H), 4.62 (d, J=5.7 Hz, 2H), 2.40 (s, 3H).

Workup

  1. customthe reaction was quenched with 10% aqueous sodium bisulfite (100 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography eluting with 17% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c34cbd5102ad496b8446ce53a951aa36
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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