Methyl chloroformate → HCID 59394985、化合物

HRID 383373

反応式

HRID 383373 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(N(CC)CC)C.Cl[C:18]([O:20][CH3:21])=[O:19]>ClCCl>[C:18](=[O:19])([O:20][CH3:21])[O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9]

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 168964-Bromo-2-methylphenol

生成物 1

HCID 59394985HCID 59394985、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Bromo-2-methyl-phenol (3.63 g, 19.41 mmol) was dissolved in dichloromethane (18 mL) and triethylamine (5.41 mL, 38.80 mmol), cooled to 0° C., then treated with methyl chloroformate (2.25 mL, 29.12 mmol) and allowed to warm to room temperature over 2 h. The reaction was quenched with water and the layers separated. The aqueous layer was extracted with dichloromethane and the combined organic extracts was dried over Na2SO4, filtered, and concentrated in vacuo to yield an oil that was purified by silica gel chromatography (10% ethyl acetate/hexane) to yield 4-bromo-2-methylphenyl methyl carbonate (4.1 g, 86% yield) as a white solid. 1H NMR (400.0 MHz, DMSO-d6) δ 7.56 (d, J=2.1 Hz, 1H), 7.44 (dd, J=2.3, 8.6 Hz, 1H), 7.18 (d, J=8.6 Hz, 1H), 3.84 (s, 3H), 2.15 (s, 3H).

後処理

  1. customThe reaction was quenched with water
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined organic extracts was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield an oil that
  8. customwas purified by silica gel chromatography (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-236f7d5495ee48bfae87437329164ba7
出典データセット
uspto-grants-2013_02
特許番号
US08367660B2

関連ノート

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