Borane → 3-(4-Bromophenyl)propan-1-ol

HRID 1530171Notes

Reaction equation

HRID 1530171 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.B>C1COCC1>[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

4

Reactant 2

HCID 6331BoraneHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

30.0 g (0.128 mol) of 3-(4-bromophenyl)propionic acid are initially introduced in 300 ml of THF, and 257 ml (0.257 mol) of a 1 M solution of boron hydride in THF are added dropwise with ice cooling. The batch is left to stir overnight at room temp., carefully hydrolysed with cooling, and extracted three times with MTB ether. The combined org. phases are washed with sat. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with MTB ether, giving 3-(4-bromophenyl)propan-1-ol, which is employed in the next step without further purification.

Workup

  1. waitThe batch is left
  2. temperaturewith cooling
  3. extractionextracted three times with MTB ether
  4. washphases are washed with sat. sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. filtrationthe residue is filtered through silica gel with MTB ether

Sources & evidence

ORD record
ord-4f04894070204443a32b1869f69bdf0b
Source dataset
uspto-grants-2015_07
Patent number
US09090822B2

Reaction notes

Loading…