Hydrogen Bromide → 1,8-Bis(bromomethyl)naphthalene

HRID 1503406노트

반응식

HRID 1503406 반응식
[C:1]1([CH2:13]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11]O)[CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.P(Br)(Br)[Br:19].[BrH:22]>O>[Br:22][CH2:13][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][Br:19])[CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 24614Phosphorus tribromideHCID 748461,8-Naphthalenedimethanol

생성물 1

HCID 2912081,8-Bis(bromomethyl)naphthalene

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A mixture of naphthalene-1,8-diyldimethanol (1.15 g, 6 mmol) and CH2Cl2 (10 mL) was stirred mechanically and PBr3 (1.2 mL) added dropwise over 20 mins. During the first half of the addition the solution refluxed spontaneously. After stirring overnight at room temperature, water was added dropwise with stirring over 20 min, which again caused refluxing and evolution of much HBr. After stirring for an additional 2 h, water was added and the layers separated and the organic layer washed with water. The organic layer was evaporated in vacuum to give the crude product, which was used directly without purification (1.6 g, 84%). 1H-NMR (CDCl3): 5.30 (s, 4H), 7.44 (m, 2H), 7.62 (m, 2H), 7.87 (m, 2H).

후처리

  1. additionDuring the first half of the addition the solution
  2. temperaturerefluxed spontaneously
  3. stirringAfter stirring overnight at room temperature
  4. stirringwith stirring over 20 min
  5. temperaturewhich again caused refluxing
  6. stirringAfter stirring for an additional 2 h
  7. customthe layers separated
  8. washthe organic layer washed with water
  9. customThe organic layer was evaporated in vacuum

출처 및 근거

ORD 기록
ord-ae78b934e26d4f948a1dcffef7d659b1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212153B2

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