4-Bromobenzaldehyde → p-Bromobenzhydryl alcohol

HRID 509177

Reaction equation

HRID 509177 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 98221p-Bromobenzhydryl alcoholYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of p-bromobenzaldehyde 10 (4 g, 21.6 mmol) in THF (20 mL) was added phenyl magnesium bromide (22.7 mL, 22.7 mmol) and the reaction mixture was stirred at room temperature for 30 minutes, quenched with water and partially concentrated under vacuum. The crude material was dissolved in ethyl acetate and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (5-45%) in hexanes to afford title compound 11 as a colorless oil (3.7 g, 65%). 1H NMR (DMSO-d6) δ (ppm): 7.49-7.45 (m, 2H), 7.36-7.17 (m, 7H), 5.98 (d, J=4.1 Hz, 1H), 5.68 (d, J=3.9 Hz, 1H).

Workup

  1. customquenched with water
  2. concentrationpartially concentrated under vacuum
  3. dissolutionThe crude material was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (5-45%) in hexanes

Sources & evidence

ORD record
ord-7bfae734ebab4c12836f611a56949d96
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Linked notes

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