Methyl chloroformate → 2-Bromo-4-tert-butylphenyl methyl carbonate

HRID 471915

反応式

HRID 471915 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].C(N(CC)CC)C.Cl[C:21]([O:23][CH3:24])=[O:22]>CN(C1C=CN=CC=1)C.ClCCl>[C:21](=[O:22])([O:23][CH3:24])[O:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:7][C:2]=1[Br:1]

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 751472-Bromo-4-tert-butylphenol

生成物 1

HCID 593949442-Bromo-4-tert-butylphenyl methyl carbonate収率 90.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2-Bromo-4-tert-butyl phenol (15.0 g, 65.5 mmol) and DMAP (400 mg, 3.3 mmol) was dissolved in dichloromethane (75 mL) and triethylamine (18.25 mL, 130.9 mmol), cooled to 0° C., then treated with methyl chloroformate (7.6 mL, 98.2 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 dried over Na2SO4. The solution was filtered and concentrated in vacuo to yield an oil that was purified by silica gel chromatography (20% ethyl acetate/hexane) to yield 2-bromo-4-tert-butylphenyl methyl carbonate (17 g, 90% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.67 (d, J=2.3 Hz, 1H), 7.47 (dd, J=2.3, 8.5 Hz, 1H), 7.33 (d, J=8.5 Hz, 1H), 3.86 (s, 3H), 1.29-1.26 (m, 9H).

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 dried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto yield an oil that
  8. customwas purified by silica gel chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-318b28e697234ca8a872b0299b5753e0
出典データセット
uspto-grants-2014_01
特許番号
US08633189B2

関連ノート

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