Bromine → 2-Bromo-4-(methylsulfonyl)phenol

HRID 1420817Notes

Reaction equation

HRID 1420817 reaction equation
[Br:1]Br.[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5]>C(O)(=O)C>[Br:1][C:11]1[CH:12]=[C:7]([S:4]([CH3:3])(=[O:5])=[O:6])[CH:8]=[CH:9][C:10]=1[OH:13]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 1233504-(Methylsulfonyl)phenol

Product 1

HCID 187826382-Bromo-4-(methylsulfonyl)phenolYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.9 ml, 17.45 mmol) in glacial acetic acid (10 ml) was added dropwise to a stirred solution of 4-(methanesulfonyl)phenol (Description 26; 3 g, 17.45 mmol). The resulting solution was stirred at ambient temperature for 16 h. Bromine (0.45 ml) in glacial acetic acid (5 ml) was added dropwise and the solution was stirred for 2 h. The excess acetic acid and bromine were removed in vacuo and the residue was azeotroped with toluene to give the desired compound as an off-white solid (3.54 g, 81%). 1H NMR (250 MHz, CDCl3) δ8.06-8.05 (1H, d, J 2.3 Hz), 7.73-7.69 (1H, dd, J 8.6, 2.3 Hz), 7.06-7.02 (1H, d, J 8.6 Hz), and 3.06 (3H, s).

Workup

  1. stirringthe solution was stirred for 2 h
  2. customThe excess acetic acid and bromine were removed in vacuo
  3. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-e45ce19ba7a948909ed5a6ce765bae79
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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