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

HRID 1465081

반응식

HRID 1465081 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 593949442-Bromo-4-tert-butylphenyl methyl carbonate수율 90.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-25f313e60f0e4ba9971b4f918394545f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999976B2

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