Ethyl 2-(4-bromophenyl)-2-methylpropanoate → 4-Bromo-beta,beta-dimethylbenzeneethanol

HRID 1043494Notes

Reaction equation

HRID 1043494 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])([CH3:14])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11277257Ethyl 2-(4-bromophenyl)-2-methylpropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 128051244-Bromo-beta,beta-dimethylbenzeneethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the material from Step 1 (2.4 g, 8.9 mmol) in 30 mL of THF at −78° C. was added LiAlH4 (337 mg, 8.9 mmol). The mixture was stirred at or below −60° C. for 2 hr, and then stirred at room temperature for 1 hr. The reaction was quenched with 10% NaOH (aq) solution, and the mixture was extracted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated to get 2-(4-bromophenyl)-2-methylpropan-1-ol (2.03 g, 100%).

Workup

  1. stirringstirred at room temperature for 1 hr
  2. customThe reaction was quenched with 10% NaOH (aq) solution
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9f60d353292407eb9d2cd6ca990ef01
Source dataset
uspto-grants-2013_10
Patent number
US08563543B2

Reaction notes

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