Boron trifluoride → 7-Bromo-1-fluoronaphthalene

HRID 891959

반응식

HRID 891959 반응식
B(F)(F)[F:2].N[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([Br:16])[CH:12]=[CH:11]2.C(ON=O)(C)(C)C>C1COCC1.C(COC)OC>[Br:16][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[C:6]([F:2])[CH:7]=[CH:8][CH:9]=2)[CH:14]=1

참가 물질

6

반응물 3

HCID 6356Boron trifluorideHCID 10906Tert-Butyl nitriteHCID 222402477-Bromonaphthalen-1-amine

생성물 1

HCID 2976587-Bromo-1-fluoronaphthalene수율 59%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 80711,2-Dimethoxyethane용매3회

실험 절차

To a solution of BF3-etherate (0.86 ml, 1.25 M in THF, 6.5 mmol) in 12 ml dimethoxyethane was added at −5° C. a solution of 8-amino-2-bromo-naphthalene (1.20 g, 5.4 mmol) in dimethoxyethane (12 ml) over a periode of 35 min. After 1 hour a solution of tert-butylnitrite (0.62 ml, 5.4 mmol) in dimethoxyethane (24 ml) was added and the mixture was stirred for two hours at r.t. and the solvent was removed under reduced pressure. Chlorbenzene (120 ml) was added and the reaction mixture was refluxed for 50 min and the mixture was concentrated. The solid was diluted in methylene chloride and washed with NaHCO3. The organic phase was dried over MgSO4, filtered and reduced to give the crude product. Chromatography on silica gel (hexane) afforded 721 mg (59%) of the product as a brown oil. MS: m/e=242 (M+).

후처리

  1. customthe solvent was removed under reduced pressure
  2. additionChlorbenzene (120 ml) was added
  3. temperaturethe reaction mixture was refluxed for 50 min
  4. concentrationthe mixture was concentrated
  5. additionThe solid was diluted in methylene chloride
  6. washwashed with NaHCO3
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. customto give the crude product

출처 및 근거

ORD 기록
ord-8eaa7b289cad472f9668180d7981272a
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005432B2

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