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

HRID 839364Notes

Reaction equation

HRID 839364 reaction equation
[Br:1]Br.[Cl:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6]>C(O)(=O)C>[Br:1][C:12]1[CH:13]=[C:8]([S:5]([CH2:4][Cl:3])(=[O:6])=[O:7])[CH:9]=[CH:10][C:11]=1[OH:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 127076294-((Chloromethyl)sulfonyl)phenol

Product 1

HCID 203243752-Bromo-4-(chloromethanesulfonyl)phenolYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

160 g (1 mole) of bromine were added dropwise at room temperature to a solution of 206.5 g (1 mole) of 4-chloromethylsulfonylphenol in 500 ml of glacial acetic acid; the mixture was stirred for a further hour at 45° C and, when it has cooled, was poured onto 1.5 l of ice-water. The product which had precipitated was filtered off and recrystallized from toluene. 185 g (65% of theory) of 2-bromo-4-chloromethylsulfonylphenol were thus obtained as a colorless powder of melting point 158°-160° C.

Workup

  1. temperaturewhen it has cooled
  2. customThe product which had precipitated
  3. filtrationwas filtered off
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-c4170d7a613842a88429580e81bdf6b7
Source dataset
uspto-grants-1978_06
Patent number
US04094975

Reaction notes

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