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

HRID 27639

Reaction equation

HRID 27639 reaction equation
[CH3:1][C:2](=[CH2:5])[CH2:3][Cl:4].[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>CCOCC>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([C:2]([CH3:5])([CH3:1])[CH2:3][Cl:4])[CH:8]=1

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)anisole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Methylallyl chloride (108 parts) was added dropwise to a mixture of 4-bromoanisole (240 parts) and a concentrated sulphuric acid (20 parts) over a period of 2 hours at a temperature of 25°-35° C. Stirring was continued for 5 hours and the mixture was then kept for 24 hours at room temperature. Ether (400 parts) was then added and the resulting solution washed with water, aqueous sodium bicarbonate solution and water again. After drying with sodium sulphate and evaporating off the solvent the brown oil which remained was distilled yielding 4-bromo-2-(2-chloro-1,1-dimethylethyl)anisole (118 parts), boiling point 106°-120°/0.4 mm Hg. Recrystallisation from petroleum ether (b.p. 80°-100° C.) gave the pure product (98 parts), melting point 86°-88° C.

Workup

  1. waitthe mixture was then kept for 24 hours at room temperature
  2. washthe resulting solution washed with water, aqueous sodium bicarbonate solution and water again
  3. dry with materialAfter drying with sodium sulphate
  4. customevaporating off the solvent the brown oil which
  5. distillationremained was distilled

Sources & evidence

ORD record
ord-266fd8a62a0a47d3a939fd2dd8df2e02
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Linked notes

Loading…