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

HRID 1155950Notes

Reaction equation

HRID 1155950 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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.)

Sources & evidence

ORD record
ord-8c1fbbcd9ce04336852ef9036ebb861f
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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