Sulfuric Acid → 4-Bromo-2-(2-chloro-1,1-dimethylethyl)anisole

HRID 444076

반응식

HRID 444076 반응식
[CH3:1][C:2]([CH2:4][Cl:5])=[CH2:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.S(=O)(=O)(O)O>ClCCl>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][C:9]=1[C:2]([CH3:3])([CH3:1])[CH2:4][Cl:5]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 77304-BromoanisoleHCID 112413-Chloro-2-methyl-1-propene

생성물 1

HCID 46057784-Bromo-2-(2-chloro-1,1-dimethylethyl)anisole수율 49.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

β-Methallyl chloride (90.5 g, 1.0 mole) was added dropwise to a stirred mixture of p-bromoanisole (200 g, 1.07 mole) and sulphuric acid (34.2 g, 0.35 mole) at 35°-40° C. over about 2 hours. After 21/2 hours at ambient temperature, the mixture was dissolved in dichloromethane, washed with water, aqueous sodium bicarbonate and water again, dried over magnesium sulphate and run down. Distillation of the residue gave a small forerun b.p. about 54° C. at 0.2 mm Hg and a main fraction of 182 g (62%) b.p. 99°-120° C. at 0.15-0.2 mm Hg. Recrystallisation from petroleum ether (b.p. 80°-100° C.) gave 137 g pure title product m.p. 82°-4° C. Reduction in volume of the mother liquors afforded a further 14 g product.

후처리

  1. washwashed with water, aqueous sodium bicarbonate and water again
  2. dry with materialdried over magnesium sulphate
  3. distillationDistillation of the residue
  4. customgave a small forerun b.p. about 54° C. at 0.2 mm Hg
  5. customRecrystallisation from petroleum ether (b.p. 80°-100° C.)

출처 및 근거

ORD 기록
ord-d984b1adecf9429c99cf63077136d4a1
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04263037

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