Acetic Acid → 2-Bromo-4-(methylsulfonyl)phenol

HRID 1496998Notes

Reaction equation

HRID 1496998 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)(=O)C.[Br:16]Br.C([O-])(O)=O.[Na+]>CCOCC>[Br:16][C:9]1[CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=1[OH:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 1233504-(Methylsulfonyl)phenolHCID 516892Sodium Bicarbonate

Product 1

HCID 187826382-Bromo-4-(methylsulfonyl)phenolYield 43.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 4-(methylsulfonyl)phenol (5 g, 29.1 mmol) in ether (100 mL) at −15° C. was slowly added acetic acid (5 mL). To this cold solution was slowly added Br2 (5.1 g, 32.0 mmol) and the reaction was stirred at −10° C. for 1 h and then warmed to r.t. and stirred for further 10 h. After the reaction was completed, 100 mL of sat. NaHCO3 aq. was added and the mixture was extracted with EA (50 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and evaporation of the solvent, 2-bromo-4-(methylsulfonyl)phenol (3.2 g, 43.6%) was obtained as a white solid.

Workup

  1. customat −15° C.
  2. temperaturewarmed to r.t.
  3. stirringstirred for further 10 h
  4. extractionthe mixture was extracted with EA (50 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-e3a3f28ea45346d68f58461fea2a4731
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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