Dibromomethane → 1-(Cyclopropylmethyl)-4-methoxybenzene

HRID 645335

반응식

HRID 645335 반응식
C(Br)Br.[C:4](Cl)(=O)C.[C:8]1([O:17][CH3:18])[CH:16]=[CH:15][C:11]([CH2:12][CH:13]=[CH2:14])=[CH:10][CH:9]=1.CC(OC)(C)C>C(OCC)C.[Zn].Cl[Cu]>[CH:13]1([CH2:12][C:11]2[CH:15]=[CH:16][C:8]([O:17][CH3:18])=[CH:9][CH:10]=2)[CH2:4][CH2:14]1

참가 물질

8

반응물 4

HCID 3024Dibromomethane2회HCID 6367Acetyl chlorideHCID 8815EstragoleHCID 15413tert-Butyl methyl ether

생성물 1

HCID 64224761-(Cyclopropylmethyl)-4-methoxybenzene수율 589.7%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매3회

반응 조건

온도
45 °C

실험 절차

CH2Br2 (220 g) was added to a slurry of zinc powder (340 g) and CuCl (54 g) in diethyl ether (450 ml). The reaction was started by the addition of acetyl chloride (8 g). The reaction mixture was heated to 45° C. and a solution of estragol (192 g) in ether (150 ml) was added during 25 minutes. Additional CH2Br2 (456 g) dissolved in ether (150 ml) was dropped into the grey-red suspension during 45 minutes. Afterwards, the mixture was stirred at 50° C. for 12 hours. The suspension was cooled to room temperature and MTBE (900 ml) was added. The mixture was filtered through celite, and the filtrate was washed with saturated NH4Cl, water, saturated NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled (b.p. 90-95° C./0.1 Torr) to yield 97.5 g (46%) of a colorless oil, which was found to have the following characteristics, NMR and MS spectra.

후처리

  1. additionwas dropped into the grey-red suspension during 45 minutes
  2. temperatureThe suspension was cooled to room temperature
  3. filtrationThe mixture was filtered through celite
  4. washthe filtrate was washed with saturated NH4Cl, water, saturated NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled (b.p. 90-95° C./0.1 Torr)

출처 및 근거

ORD 기록
ord-30f4661058b54a008d52b9a20ce7ef92
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704942B2

연결된 노트

불러오는 중…