Methyl iodide → 1-Bromo-4-chloro-2-fluoro-3-methoxybenzene

HRID 1363926

반응식

HRID 1363926 반응식
[Br:1][C:2]1[C:3]([F:10])=[C:4]([OH:9])[C:5]([Cl:8])=[CH:6][CH:7]=1.CI.[C:13](=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([O:9][CH3:13])[C:3]=1[F:10]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666010023-Bromo-6-chloro-2-fluorophenol

생성물 1

HCID 666003671-Bromo-4-chloro-2-fluoro-3-methoxybenzene수율 96.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A heterogeneous mixture of 3-bromo-6-chloro-2-fluorophenol (14.4 g, 0.064 mol), methyl iodide (13.5 g, 0.096 mol) and potassium carbonate (8.8 g, 0.064 mol) in acetonitrile (100 mL) was heated under reflux for two hours. The mixture was cooled, diluted with water (100 mL) and extracted with diethyl ether (2×150 mL). The combined extracts were dried and concentrated. The dark oil was purified by chromatography (5% ethyl acetate in hexanes) to give 1-bromo-4-chloro-2-fluoro-3-methoxybenzene (14.8 g, 0.062 mol) 1H NMR (CDCl3): δ 7.20 (m, 1H), 7.10 (dd, 1H), 4.0 (s, 3H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether (2×150 mL)
  5. customThe combined extracts were dried
  6. concentrationconcentrated
  7. customThe dark oil was purified by chromatography (5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-805d86e95dee42e592b64392dac9fa31
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888287B2

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