Methyl 4-bromo-3-methylbenzoate → (4-Bromo-3-methylphenyl)methanol

HRID 9631

Reaction equation

HRID 9631 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[CH3:11]

Participants

5

Reactant 2

HCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl-4-bromo-3-methylbenzoate (4.31 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to 0° C. under nitrogen gas. A solution of 1.5M diisobutylaluminium hydride in toluene (44 ml) was added slowly and the reaction stirred for 2.5 hours, then quenched with methanol and allowed to warm to 21° C. Silica was added and the reaction concentrated in vacuo and purified using SPE (Si cartridge) using cyclohexane:ethyl acetate (3:1) as an eluent which furnished the title compound as a brown oil.

Workup

  1. customquenched with methanol
  2. temperatureto warm to 21° C
  3. additionSilica was added
  4. concentrationthe reaction concentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-daad5c5a6a204b0ea960dce434566389
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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