Hydrochloric Acid → 4-Bromo-2-chlorobenzenesulfonyl chloride

HRID 2215106Notes

Reaction equation

HRID 2215106 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([Cl:9])[CH:3]=1.[ClH:10].N([O-])=O.[Na+].[S:15](=[O:17])=[O:16]>C(O)(=O)C.O.[Cu]>[Cl:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:8]=[CH:7][C:5]=1[S:15]([Cl:10])(=[O:17])=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 6101694-Bromo-2-chloroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27347664-Bromo-2-chlorobenzenesulfonyl chloride

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A stirred solution of 4-bromo-2-chloroaniline (3.99 g) in acetic acid (90 ml) at 15° C. is treated with concentrated hydrochloric acid (22 ml), followed by a solution of sodium nitrite (1.29 g) in water (4.5 ml) at 10° C. After 30 min, the mixture is added to a stirred solution of sulfur dioxide (32 g) and copper II chloride (1.3 g) in acetic acid (128 ml) and water (6.4 ml), also at 10° C. After stirring for a further 16 hours, the mixture is diluted with ice-cold water (500 ml) and extracted with ethyl acetate (4×100 ml). The combined extracts are washed successively with water (4×100 ml) and then brine, dried over magnesium sulfate, filtered and evaporated to give crude 2-chloro-4-bromobenzenesulfonyl chloride.

Workup

  1. extractionextracted with ethyl acetate (4×100 ml)
  2. washThe combined extracts are washed successively with water (4×100 ml)
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ebdb7df379c0446280fcf32807156fda
Source dataset
uspto-grants-2006_09
Patent number
US07109203B2

Reaction notes

Loading…