3,4,5,6-Tetrahydrophthalic anhydride → 3-(3-Bromo-4-fluoro-benzylidene)-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

HRID 1012952

반응식

HRID 1012952 반응식
[C:1]1(=[O:11])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3](=O)[O:2]1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:20]C(O)=O)[CH:16]=[CH:17][C:18]=1[F:19].C([O-])(=O)C.[Na+]>>[Br:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:18]=1[F:19])[CH:20]=[C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[C:1](=[O:11])[O:2]1

참가 물질

4

반응물 3

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 517045Sodium AcetateHCID 34163393-Bromo-4-fluorophenylacetic Acid

생성물 1

HCID 675241363-(3-Bromo-4-fluoro-benzylidene)-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

실험 절차

4,5,6,7-tetrahydro-isobenzofuran-1,3-dione (7) (16.7 g, 109.7 mmol) and 3-bromo-4-fluorophenylacetic acid (15.0 g, 64.37 mmol) were heated in the presence of sodium acetate (0.259 g, 3.160 mmol) to 210° C. using a ‘Wood's Alloy’ bath for 4.5 hours. The reaction mixture was then poured into a crucible and cooled to give a crystalline solid. The solid was ground with a mortar and pestle and triturated with ethanol (20 ml). The resultant suspension was then filtered and washed with further ethanol (10 ml). The solid was then dried to afford the desired product as a mixture of geometric isomers. Main peak in LC-MS, (20.78 g, 94% purity) and required no further purification; m/z (LC-MS, ESP), RT=4.74 mins (no ionization observed).

후처리

  1. customfor 4.5 hours
  2. additionThe reaction mixture was then poured into a crucible and
  3. temperaturecooled
  4. customto give a crystalline solid
  5. customtriturated with ethanol (20 ml)
  6. filtrationThe resultant suspension was then filtered
  7. washwashed with further ethanol (10 ml)
  8. customThe solid was then dried

출처 및 근거

ORD 기록
ord-feca037d72c54cec85bcb025dd40f053
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981890B2

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