Ethyl 4-bromocinnamate → 2-Propen-1-ol, 3-(4-bromophenyl)-, (2E)-

HRID 1590378Notes

Reaction equation

HRID 1590378 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8](OCC)=[O:9])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][OH:9])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 141107Ethyl 4-bromocinnamateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 533963712-Propen-1-ol, 3-(4-bromophenyl)-, (2E)-Yield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4 -bromocinnamate (12.12 g) was dissolved in dry dichloromethane (50 ml) under nitrogen and cooled to -20°. Diisobutylaluminium hydride (100 ml, 1M solution in dichloromethane) (ex Aldrich) was added dropwise. The solution was allowed to warm to 25° then stirred for 18 hours then partitioned between ether and dilute hydrochloric acid. The organic phase was washed with saturated sodium bicarbonate, brine, dried over magnesium sulphate and concentrated under vacuum to give 3-(4-bromophenyl)prop-2-en-1-ol (8.9 g). NMR 1H: 7.28(2H,d), 7.05 (2H,d), 6.45 (1H,d), 6.25 (1H,t), 4.25 (2H,d), 2.0 (1H,s).

Workup

  1. temperaturecooled to -20°
  2. temperatureto warm to 25°
  3. customthen partitioned between ether and dilute hydrochloric acid
  4. washThe organic phase was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7d9b2d90cf8a469596d12bcca3003d5f
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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