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

HRID 444076

反応式

HRID 444076 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-d984b1adecf9429c99cf63077136d4a1
出典データセット
uspto-grants-1981_04
特許番号
US04263037

関連ノート

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