Water → 2-(3,4-Dihydroxyphenyl)acetonitrile

HRID 401535

반응식

HRID 401535 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]#[N:12])[CH:7]=[CH:6][C:5]=1[OH:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 781783,4-(Methylenedioxy)phenylacetonitrile

생성물 1

HCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile수율 54.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzo[1,3]dioxol-5-yl-acetonitrile (0.50 g, 3.1 mmol) in CH2Cl2 (15 mL) was added dropwise BBr3 (0.78 g, 3.1 mmol) at −78° C. under N2. The mixture was slowly warmed to room temperature and stirred overnight. H2O (10 mL) was added to quench the reaction and the CH2Cl2 layer was separated. The aqueous phase was extracted with CH2Cl2 (2×7 mL). The combined organics were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1) to give (3,4-dihydroxy-phenyl)-acetonitrile (0.25 g, 54%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.07 (s, 1H), 8.95 (s, 1H), 6.68-6.70 (m, 2H), 6.55 (dd, J=8.0, 2.0 Hz, 1H), 3.32 (s, 2H).

후처리

  1. customto quench
  2. customthe reaction
  3. customthe CH2Cl2 layer was separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×7 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. custompurified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

출처 및 근거

ORD 기록
ord-db38382a874e4a3abc5f2cdbce8c17a5
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741933B2

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