1-(4-Bromophenyl)cyclobutane-1-carboxylic acid → (1-(4-Bromophenyl)cyclobutyl)methanol

HRID 1054739

반응식

HRID 1054739 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acid

생성물 1

HCID 58538689(1-(4-Bromophenyl)cyclobutyl)methanol수율 62%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1-(4-bromophenyl)cyclobutanecarboxylic acid (300 mg, 1.20 mmol) in 1,4-dioxane (5 mL) was added borane dimethylsulfide complex (0.24 mL, 2.4 mmol) dropwise at 0° C. The ice bath was removed, and the reaction mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with methanol (20 mL). The organic solvents were removed under reduced pressure to give a residue, which was dissolved in ethyl acetate, then washed with brine. The organic phase was concentrated to give [1-(4-bromophenyl)cyclobutyl]methanol (170 mg, 62% yield) as a yellow oil which was used directly in the next step.

후처리

  1. customThe ice bath was removed
  2. customThe reaction mixture was quenched with methanol (20 mL)
  3. customThe organic solvents were removed under reduced pressure
  4. customto give a residue, which
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

출처 및 근거

ORD 기록
ord-a43ab158e3014363b8dc7631e25448f1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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