Sulfuric Acid → HCID 58137421, compound

HRID 1055641Notes

Reaction equation

HRID 1055641 reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].FF.S(=O)(=O)(O)O.[Br:23]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[Br:23][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])[CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24524FluorineHCID 67184N-bromobutanimideHCID 27792093-(Pentafluorosulfanyl)benzoic acid

Product 1

HCID 58137421HCID 58137421, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

150 g (604 mmol) of 3-(pentafluoro-λ6-sulphanyl)benzoic acid [lit. e.g.: C. Zarantonello et al., J. Fluorine Chem. 2007, 128 (12), 1449-1453; WO 2005/047240-A1; also available commercially] were initially charged in 300 ml of trifluoroacetic acid, and 90 ml of concentrated sulphuric acid were added. 161.4 g (907 mmol) of N-bromosuccinimide (NBS) were added to the resulting clear solution. The reaction mixture was then stirred at a temperature of 50° C. overnight (about 18 h). After cooling to RT, the mixture was carefully stirred into about 2.25 liters of ice water. The precipitated product was filtered off with suction, washed with water and dried under high vacuum. This gave 193 g (96% of theory, 98% pure) of the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationThe precipitated product was filtered off with suction
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-bfc2a322d8a84ca7a1fbfbcfce746524
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

Loading…