2-Amino-3,5-dibromobenzene-1-sulfonyl fluoride → 2,4-Dibromo-6-(methanesulfonyl)aniline

HRID 1995456Notes

Reaction equation

HRID 1995456 reaction equation
F[S:2]([C:5]1[CH:11]=[C:10]([Br:12])[CH:9]=[C:8]([Br:13])[C:6]=1[NH2:7])(=[O:4])=[O:3].[CH3:14][Li]>CCOCC>[Br:13][C:8]1[CH:9]=[C:10]([Br:12])[CH:11]=[C:5]([S:2]([CH3:14])(=[O:4])=[O:3])[C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 132189042-Amino-3,5-dibromobenzene-1-sulfonyl fluorideHCID 178418348HCID 178418348, compound

Product 1

HCID 132189052,4-Dibromo-6-(methanesulfonyl)aniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-fluorosulfonyl-4,6-dibromoaniline (7.19 g; 0.0216 mol) in ether (100 ml) is cooled to -65° C. under a nitrogen atmosphere and a solution of methyllithium in ether (37.5 ml of 1.8 M; 0.0675 mol) is added via a syringe. The mixture is allowed to warm to 0° C., the solution is poured into ice, and the ether layer is separated. The aqueous layer is extracted with ether (3×100 ml) and the ether layers are combined. The solvent is removed under reduced pressure and the residue crystallized from petroleum ether to afford the title product.

Workup

  1. additionthe solution is poured into ice
  2. customthe ether layer is separated
  3. extractionThe aqueous layer is extracted with ether (3×100 ml)
  4. customThe solvent is removed under reduced pressure
  5. customthe residue crystallized from petroleum ether

Sources & evidence

ORD record
ord-74c4c2aef08e4151943501baf933121d
Source dataset
uspto-grants-1983_09
Patent number
US04404402

Reaction notes

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