Bromoacetic Acid → 1,2,4-Trifluoro-5-(methylsulfonyl)benzene

HRID 20554

Reaction equation

HRID 20554 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].S([O-])([O-])=O.[Na+].[Na+].[C:20](=O)(O)[O-].[Na+].BrCC(O)=O>O>[F:9][C:5]1[CH:4]=[C:3]([S:10]([CH3:20])(=[O:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27769792,4,5-Trifluorobenzenesulfonyl chloride

Product 1

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

2,4,5-Trifluorophenyl sulfonyl chloride (279 mg) was added to a solution of sodium sulfite (306 mg) and sodium bicarbonate (153 mg) in water (4 mL). The mixture was heated to 150° C. in a sealed microwave vial for 400 seconds and allowed to cool. The mixture was treated with bromoacetic acid (253 mg) in water (1 mL), and heated to 150° C. for 300 seconds then allowed to cool, following which the precipitate was removed by filtration and dried in vacuo to give the desired compound (169 mg). The material was used without further purification. 1H NMR δ (d6-DMSO): 3.35 (s, 3H), 7.87-8.01 (m, 2H).

Workup

  1. temperatureto cool
  2. temperatureheated to 150° C. for 300 seconds
  3. temperatureto cool
  4. customwas removed by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e9d217611dd942d58da602e9cc758320
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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