Potassium Carbonate → 3-(4-Bromophenyl)propan-1-ol

HRID 2354289Notes

Reaction equation

HRID 2354289 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.O1CCCC1.B.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Procedure

To a solution of 3-(4-bromophenyl)propionic acid (1.0 g) in tetra hydrofuran (15 mL) was added borane tetra hydrofuran complex (1.0 mol/L tetra hydrofuran solution, 6.55 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 20% aqueous potassium carbonate solution under ice-cooling, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 3-(4-bromophenyl)propanol (0.93 g). The title compound was prepared in a similar manner to that described in Reference Example 55 using this material instead of 2-(4-bromo-phenyl)ethanol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe resulting mixture was extracted with ethylacetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c421cc4fe4ea460f8e8ab435f6d671b9
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

Loading…