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

HRID 468232

反応式

HRID 468232 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile収率 54.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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/ethyl acetate 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).

後処理

  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/ethyl acetate 5:1)

出典と根拠

ORDレコード
ord-53197e07b8344c7d91022f5e7ff4ae79
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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