Boron trifluoride etherate → 8-Fluoro-1-tetralone

HRID 9262

반응식

HRID 9262 반응식
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2.B(F)(F)[F:14].CCOCC.N(OC(C)(C)C)=O>C(Cl)Cl.CCCCC>[F:14][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2

참가 물질

6

반응물 3

HCID 8000Boron trifluoride etherateHCID 10906Tert-Butyl nitriteHCID 114009428-Amino-1-tetralone

생성물 1

HCID 112521888-Fluoro-1-tetralone

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8003Pentane용매

반응 조건

온도
0 °C

실험 절차

The amine (Intermediate J3, 1.83 g, 11.3 mmol) in CH2Cl2 (17 mL) was added to BF3.OEt2 (2.80 mL, 22.1 mmol) at −15° C. More CH2Cl2 (20 mL) was added to the precipitate. Next, t-butyl nitrite (1.8 mL, 12.9 mmol) in CH2Cl2 (20 mL) was added at −15° C. and stirred for 10 min. and at 0° C. for 20 m. The mixture was diluted with pentane (40 mL), filtered and the solids were collected, washed with ether, and dried under vacuum. The solids were placed in a flask and heated to 115° C. for 10–15 min. followed by addition of 2N NaOH and CHCl3. The suspension was filtered and the aqueous phase was extracted with CHCl3. The organic layers were combined, dried over MgSO4, filtered and purified by chromatography on SiO2 with 15% EtOAc:Hx. The product, 8-fluoro-3,4-dihydro-2H-naphthalen-1-one (Intermediate J4) was isolated; 750 mg (40%).

후처리

  1. filtrationfiltered
  2. customthe solids were collected
  3. washwashed with ether
  4. customdried under vacuum
  5. customThe solids were placed in a flask
  6. temperatureheated to 115° C. for 10–15 min.
  7. additionfollowed by addition of 2N NaOH and CHCl3
  8. filtrationThe suspension was filtered
  9. extractionthe aqueous phase was extracted with CHCl3
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. custompurified by chromatography on SiO2 with 15% EtOAc

출처 및 근거

ORD 기록
ord-a8ca59da901b4226a81b5c7540f40e6a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091232B2

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