Ethyl 2-(4-bromophenyl)propanoate → 2-(4-Bromophenyl)propan-1-ol

HRID 735687Notes

Reaction equation

HRID 735687 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13840376Ethyl 2-(4-bromophenyl)propanoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 5690622-(4-Bromophenyl)propan-1-olYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 73A (3.06 g, 11.9 mmol) in 50 mL CH2Cl2 at −78° C., was added a solution of diisobutylaluminum hydride (35.7 mL, 35.7 mmol, 1M in hexanes). The mixture was removed from the cooling bath, stirred 1 h, then recooled to −50° C. and quenched with EtOAc (2 mL). The reaction mixture was diluted with H2O, then extracted with EtOAc (3×). The combined organic extract washed with brine, dried (Na2SO4), filtered through a 1″ pad of SiO2, then concentrated to afford 2.34 g of 73B as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+.

Workup

  1. customThe mixture was removed from the cooling bath
  2. customrecooled to −50° C.
  3. customquenched with EtOAc (2 mL)
  4. additionThe reaction mixture was diluted with H2O
  5. extractionextracted with EtOAc (3×)
  6. extractionThe combined organic extract
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered through a 1″ pad of SiO2
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bd03e5fab0324f5eb002df79d4521b01
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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