Boron trifluoride etherate → 8-Fluoro-1-tetralone

HRID 560039

反応式

HRID 560039 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 112521888-Fluoro-1-tetralone

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8003Pentane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1968b605de524093b1f508e88aeb4273
出典データセット
uspto-grants-2011_11
特許番号
US08063087B2

関連ノート

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