4-Bromobenzaldehyde → p-Bromobenzhydryl alcohol

HRID 509177

반응식

HRID 509177 반응식
[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

참가 물질

4

반응물 2

HCID 707414-BromobenzaldehydeHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 98221p-Bromobenzhydryl alcohol수율 65.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7bfae734ebab4c12836f611a56949d96
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096565B2

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