N-Iodosuccinimide → 2-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

HRID 1619696ノート

反応式

HRID 1619696 の反応式
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]>S(=O)(=O)(O)O.C(O)(=O)C.ClCCl>[Cl:9][C:10]1[CH:15]=[C:14]([I:1])[C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]

参加物

6

反応物 2

HCID 120273N-IodosuccinimideHCID 580422982-Chloro-2'-fluoro-5-methoxybiphenyl

生成物 1

HCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl収率 60.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

N-Iodosuccinimide (683 mg, 3.04 mmol) was added to a solution of 2-chloro-2′-fluoro-5-methoxybiphenyl (Preparation 96, 749 mg, 3.16 mmol) in concentrated sulfuric acid (0.09 mL), acetic acid (4.7 mL) and dichloromethane (4.7 mL). The resulting mixture was stirred at room temperature for 18 hours and then partitioned between dichloromethane (30 mL) and water (5 mL). The organic phase was separated and washed with water (2×5 mL), brine (5 mL), dried over MgSO4, filtered and evaporated to give a red oil. Column chromatography purification on silica, eluting with dichloromethane:heptanes (1:9) gave the title compound (671 mg, 58%) as a colourless oil.

後処理

  1. custompartitioned between dichloromethane (30 mL) and water (5 mL)
  2. customThe organic phase was separated
  3. washwashed with water (2×5 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customColumn chromatography purification on silica
  9. washeluting with dichloromethane:heptanes (1:9)

出典と根拠

ORDレコード
ord-d62db1b14fc1499eb54ec3a4b2cc7148
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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