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

HRID 1012952

反応式

HRID 1012952 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-feca037d72c54cec85bcb025dd40f053
出典データセット
uspto-grants-2011_07
特許番号
US07981890B2

関連ノート

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