Hydrogen Bromide → 6-Bromo-1-tetralone

HRID 537747

반응식

HRID 537747 반응식
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.N([O-])=O.[Na+].[BrH:17]>O.[Cu]Br>[Br:17][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

참가 물질

6

반응물 3

HCID 260Hydrogen Bromide2회HCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23668193Sodium Nitrite

생성물 1

HCID 101050696-Bromo-1-tetralone

시약·촉매·용매 2

HCID 24593copper(I) bromide촉매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of 6-amino-3,4-dihydro-2H-naphthalen-1-one (20.5 g, 127 mmol) in 25% HBr (aq) (1017 ml) at 0° C. was added a solution of sodium nitrite (10.53 g, 153 mmol) in water (50 ml) dropwise at a rate as to maintain the temperature below 3°. The cooled reaction mixture was then added to a cooled solution of copper(I) bromide (18.79 g, 131 mmol) in HBr (98 ml, 865 mmol). When the addition was done, the reaction mixture was stirred at 0° C. for 1 h, then warmed to rt. Water (380 mL) was added and the product was extracted with a mixture of Et2O/EtOAc (8:2, 3×). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give a dark brown crude oil. The crude was purified by distillation (3 mm Hg) to give 16.415 g of 6-bromo-3,4-dihydro-2H-naphthalen-1-one.

후처리

  1. temperatureto maintain the temperature below 3°
  2. customThe cooled reaction mixture
  3. additionWhen the addition
  4. temperaturewarmed to rt
  5. extractionthe product was extracted with a mixture of Et2O/EtOAc (8:2, 3×)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a dark brown crude oil
  10. distillationThe crude was purified by distillation (3 mm Hg)

출처 및 근거

ORD 기록
ord-8250d8215efc4d1f8c8ced1ec71915f9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865701B2

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