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

HRID 724711Notes

Reaction equation

HRID 724711 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[CH3:12].[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 4148881Lithium borohydride

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-bromo-3-methylbenzoate (50.0 g, 218 mmol), lithium tetrahydroborate (5.70 g, 262 mmol) and tetrahydrofuran (500 mL) was stirred at 25° C. for 2 d. The reaction was cooled to 0° C., quenched with saturated NH4Cl solution and diluted with ethyl acetate. The aqueous layers were extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (36.0 g, 82%).

Workup

  1. customquenched with saturated NH4Cl solution
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layers were extracted with ethyl acetate three times
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f03648f997044d41af0e614b448afe8f
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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