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

HRID 495016

反応式

HRID 495016 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 666003671-Bromo-4-chloro-2-fluoro-3-methoxybenzene収率 96.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4bd1fd11c85f47bba1e23f442a4380fa
出典データセット
uspto-grants-2009_05
特許番号
US07538214B2

関連ノート

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