Methyl iodide → 1-Bromo-2,5-dichloro-4-methoxybenzene

HRID 1930124

반응식

HRID 1930124 반응식
CI.[Br:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([OH:11])=[C:6]([Cl:12])[CH:5]=1.[C:13](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([O:11][CH3:13])=[CH:8][C:9]=1[Cl:10]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160224-Bromo-2,5-dichlorophenol

생성물 1

HCID 596276791-Bromo-2,5-dichloro-4-methoxybenzene수율 75.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

Methyl iodide (1.861 mL, 29.76 mmol) was added to a stirred suspension of 4-bromo-2,5-dichlorophenol (4.8 g, 19.84 mmol) and potassium carbonate (8.23 g, 59.53 mmol) in DMF (20 mL) at ambient temperature under air. The resulting suspension was stirred at 50° C. for 90 minutes. The reaction mixture was allowed to cool and diluted with EtOAc (200 mL), and washed sequentially with saturated brine (2×150 mL) and water (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 1-bromo-2,5-dichloro-4-methoxybenzene (3.82 g, 75%) as a brown solid.

후처리

  1. temperatureto cool
  2. washwashed sequentially with saturated brine (2×150 mL) and water (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-07898fae731b40b6869cec5c39700bdb
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188092B2

연결된 노트

불러오는 중…