Boron tribromide → 1-(4-Hydroxyphenyl)cyclohexane-1-carbonitrile

HRID 272860

반응식

HRID 272860 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile

생성물 1

HCID 198585061-(4-Hydroxyphenyl)cyclohexane-1-carbonitrile수율 91.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (2 g, 9.29 mmol) in DCM (40 mL) at 0° C. under N2 was added dropwise BBr3 (2.63 mL, 27.87 mmol). The reaction was allowed to warm to room temperature and stirred for 48 hours. The mixture was stirred for 3 hours at 0° C. and quenched with water (30 mL). The mixture was separated and the organic layer was washed with a saturated aqueous solution of NaHCO3 then water. The combined organic extracts were dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel eluting with DCM:acetone (97:3) to give the title compound (1.71 g, 91%).

후처리

  1. stirringThe mixture was stirred for 3 hours at 0° C.
  2. customquenched with water (30 mL)
  3. customThe mixture was separated
  4. washthe organic layer was washed with a saturated aqueous solution of NaHCO3
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography on silica gel eluting with DCM:acetone (97:3)

출처 및 근거

ORD 기록
ord-645e7e4544bb403d8197706a894d9e71
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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