Benzoic Acid → 4-Bromo-5-(chlorosulfonyl)-2-methoxybenzoic acid

HRID 652761Notes

Reaction equation

HRID 652761 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].C(O)(=O)C1C=CC=CC=1.[Cl:22][S:23](O)(=[O:25])=[O:24]>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([Br:12])[C:9]([S:23]([Cl:22])(=[O:25])=[O:24])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 24638Chlorosulfonic acidHCID 134507554-Bromo-2-methoxybenzoic acid

Product 1

HCID 221014544-Bromo-5-(chlorosulfonyl)-2-methoxybenzoic acid

Conditions

Temperature
80 °C

Procedure

300 ml of chlorosulphonic acid of density 1.766 (4.55 mole) is placed in a 1 liter flask fitted with an agitator, a thermometer and a condenser, and 69.3 g of 2-methoxy-4-bromobenzoic acid (0.30 mole) is added in stages. The reaction is slightly exothermic and the temperature reaches 40° C. by the time all the benzoic acid has been added. The reaction medium is heated to 80° C. then returned to room temperature. The solution, which is brown, is poured slowly over 2 kg of crushed ice.

Workup

  1. customfitted with an agitator
  2. customreaches 40° C. by the time
  3. additionhas been added
  4. customthen returned to room temperature

Sources & evidence

ORD record
ord-91ce351cdeb54c009bef4609d79d6f24
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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