Dibromomethane → 1-(Cyclopropylmethyl)-4-methoxybenzene

HRID 645335

反応式

HRID 645335 の反応式
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

参加物

8

反応物 4

HCID 3024Dibromomethane2 回HCID 6367Acetyl chlorideHCID 8815EstragoleHCID 15413tert-Butyl methyl ether

生成物 1

HCID 64224761-(Cyclopropylmethyl)-4-methoxybenzene収率 589.7%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
45 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-30f4661058b54a008d52b9a20ce7ef92
出典データセット
uspto-grants-2010_04
特許番号
US07704942B2

関連ノート

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