Water → [3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-iodophenyl)-methanone

HRID 346973ノート

反応式

HRID 346973 の反応式
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:22]=1)=[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[O:13][N:14]=2.[I:23][C:24]1[CH:35]=[CH:34][C:27]([C:28](N(OC)C)=[O:29])=[CH:26][CH:25]=1.O>C1COCC1>[Cl:21][C:17]1[CH:16]=[C:15]([C:12]2[O:13][N:14]=[C:10]3[CH:9]=[CH:8][C:7]([C:28]([C:27]4[CH:34]=[CH:35][C:24]([I:23])=[CH:25][CH:26]=4)=[O:29])=[CH:22][C:11]=23)[CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 54617564-Iodo-N-methoxy-N-methyl-benzamideHCID 120166705-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazoleHCID 178418339Butyllithium

生成物 1

HCID 21082022[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-iodophenyl)-methanone収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

BuLi 1.6M (0.106 mol) was added dropwise at −70° C. to a solution of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.0816 mol), obtained in Example A1a, in THF (250 ml) under N2 flow. The mixture was stirred at −70° C. for 15 min. A solution of 4-iodo-N-methoxy-N-methyl-benzamide (0.098 mol) in THF (150 ml) was added dropwise at −70° C. The mixture was stirred at −70° C. for 1 hour then brought to room temperature. The mixture was hydrolysed with water, extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (48 g) was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 16.5 g (44%) of [3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl](4-iodophenyl)-methanone, mp.196° C. (intermediate 35).

後処理

  1. stirringThe mixture was stirred at −70° C. for 1 hour
  2. customthen brought to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue (48 g) was crystallized from diethyl ether
  9. filtrationThe precipitate was filtered off
  10. customdried

出典と根拠

ORDレコード
ord-7d80e18f5eef4bf4b208f9fb9065299c
出典データセット
uspto-grants-2007_02
特許番号
US07173040B2

反応ノート

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