Sodium Hydroxide → 4-(3-Bromophenyl)butan-1-ol

HRID 30563Notes

Reaction equation

HRID 30563 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][CH:7]=1.[H]1[BH2][H][BH2]1.C1COCC1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 183294554-(3-Bromophenyl)butanoic acid

Product 1

HCID 218954894-(3-Bromophenyl)butan-1-olYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of 4-(3-bromophenyl)butyric acid (2.85 g, 11.7 mmol) in THF was treated slowly with a solution of B2H6-THF (35 mL), stirred at room temperature for 18 hours, poured into ice/water, basified with 2.5 N NaOH to pH=11 and extracted with CH2Cl2. The extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by column chromatography using hexanes/CH2Cl2/MeOH (4/4.5/0.5) as the eluting solvent afforded 4-(3-bromophenyl)butan-1-ol as a colorless oil (1.9 g, 70% yield. m/e (M)+ 228; 1H NMR (400 MHZ, DMSO-d6) δ ppm, 1.3-1.4 (m, 2 H) 1.5-1.6 (m, 2 H), 2.55-2.59 (m, 2 H), 3.3-3.38 (m, 2H), 4.3 (t, J=7.5, 1H), 7.2-7.2 (m, 1 H), 7.3 (t, J=7.5 Hz, 1 H), 7.4-7.4 (m, 1 H), 7.4-7.4 (m, 1 H).

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the resultant residue by column chromatography

Sources & evidence

ORD record
ord-ac5469b39dd14c7abce62b4a2468f681
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

Loading…