Boron trifluoride etherate → Dibenz[b,e]oxepin-11(6H)-one

HRID 1946648

반응식

HRID 1946648 반응식
[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC>C(Cl)Cl>[CH:4]1[C:3]2[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][O:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 697612-(Phenoxymethyl)benzoic acid

생성물 1

HCID 78259Dibenz[b,e]oxepin-11(6H)-one수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

The 2-(phenoxymethyl)benzoic acid (22.18 g, 97 mmol) was dissolved in DCM (200 mL) and trifluoroacetic anhydride (20.59 mL, 146 mmol) was added, followed by a catalytic amount of borontrifluoride etherate (2.22 mL, 17.5 mmol). The reaction mixture was heated at 40° C. for 2 hours. The solution was then washed with water, sodium bicarbonate (saturated solution) and water. The organic phases was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified on silica gel (10-20% ethyl acetate in hexanes) to afford title compound 482 (19.937 g, 98%) as a light pink solid. MS (m/z): 211.1 (M+H).

후처리

  1. washThe solution was then washed with water, sodium bicarbonate (saturated solution) and water
  2. dry with materialThe organic phases was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on silica gel (10-20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-1a116199bdfc4aa1ba3fae8ed73bdf21
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399452B2

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