Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)- → (5-Iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

HRID 18671

反応式

HRID 18671 の反応式
[I:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.CC([O-])(C)C.[K+].[O-]C1C=CC=CC=1.[C:27]([CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)#[N:28]>C1COCC1>[I:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:29][C:27]#[N:28]

参加物

6

反応物 4

HCID 84525Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-HCID 119047PhenolateHCID 23665647Potassium tert-butoxideHCID 442488545-Iodo-2-isopropyl-4-methoxyphenol

生成物 1

HCID 44248984(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a cold (1 degree C.) solution of 10.0 g of 5-iodo-2-isopropyl-4-methoxy-phenol in 25 mL THF was added 41.3 mL of 1N KOtBu in THF at a rate such that the internal temperature did not exceed 6 degrees C. To the resultant phenoxide solution was added a solution of 7.2 g of toluene-4-sulfonic acid cyanomethyl ester in 25 mL THF, and the reaction mixture was allowed to warm slowly to ambient temperature overnight. The reaction mixture was partitioned between n-heptane (50 mL) and water (50 mL), and the organic layer was displaced into n-heptane by distillation (to a pot temperature of 97 degrees C.). The concentrate in n-heptane was cooled slowly to ambient temperature and the resulting crystalline solid was washed with n-heptane and dried. In this manner, 9.26 g of (5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile was isolated (81%): m.p. 67.5-68.8 degrees C.; 1H nmr (DMSO) delta: 1.18 (d, 6H, J=6.9 Hz), 3.19 (septet, 1H, J=6.9 Hz), 3.81 (s, 3H), 5.16 (s 2H), 6.88 (s, 1H), 7.50 (s, 1H).

後処理

  1. customdid not exceed 6 degrees C
  2. customThe reaction mixture was partitioned between n-heptane (50 mL) and water (50 mL)
  3. distillationthe organic layer was displaced into n-heptane by distillation (to a pot temperature of 97 degrees C
  4. concentrationThe concentrate in n-heptane
  5. temperaturewas cooled slowly to ambient temperature
  6. washthe resulting crystalline solid was washed with n-heptane
  7. customdried

出典と根拠

ORDレコード
ord-150a6b8f1f4845b28c74e8942d562525
出典データセット
uspto-grants-2010_06
特許番号
US07741484B2

関連ノート

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