Sulfuric Acid → 4-Bromo-2-(2-chloro-1,1-dimethyl-ethyl)-5-methyl-phenol

HRID 2290145Notes

Reaction equation

HRID 2290145 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[CH:9][CH:8]=1.[Cl:15][CH2:16][C:17]([CH3:19])=[CH2:18]>O>[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([C:17]([CH3:19])([CH3:18])[CH2:16][Cl:15])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 112413-Chloro-2-methyl-1-propeneHCID 728574-Bromo-m-cresol2×

Product 1

HCID 186991894-Bromo-2-(2-chloro-1,1-dimethyl-ethyl)-5-methyl-phenolYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (1.75 g, 17.8 mmol) was added drop wise to a cooled (ice bath) mixture of 4-bromo-5-methyl-phenol (Compound 45, 10 g, 53.46 mmol) and 3-chloro-2-methyl-propene (5.28 mL, 53.46 mmol). The dark reaction mixture was allowed to warm to ambient temperature and stirred a total of 2 hours. The reaction mixture was diluted with water, and extracted with diethylether. The combined organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash column chromatography using 3% ethyl acetate in hexanes as the eluent afforded the title compound (6.2 g, 48%) as a green solid; 4-bromo-5-methyl-phenol was recovered. 1H NMR (300 MHz, CDCl3): δ 7.35 (s, 1H), 6.54 (s, 1H), 5.02 (s, 1H), 3.96 (s, 2H), 2.28 (s, 3H), 1.44 (s, 6H).

Workup

  1. temperaturea cooled
  2. customThe dark reaction mixture
  3. extractionextracted with diethylether
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated to an oil

Sources & evidence

ORD record
ord-80bd4c451aa442fd9e04bf1d76b05287
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

Loading…