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

HRID 1619696노트

반응식

HRID 1619696 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d62db1b14fc1499eb54ec3a4b2cc7148
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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