Hydrochloric Acid → 3-Methoxy-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

HRID 1055648Notes

Reaction equation

HRID 1055648 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:17][O-].[Na+].CI.Cl>CO>[CH3:17][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 581367943-Hydroxy-5-(pentafluorosulfanyl)benzoic acid

Product 1

HCID 896997173-Methoxy-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
120 °C

Procedure

150 mg (0.57 mmol) of the compound of Example 24A were dissolved in 1.5 ml of methanol, 0.25 ml (1.14 mmol) of a 25% strength solution of sodium methoxide in methanol and 0.04 ml (0.62 mmol) of methyl iodide were added and the mixture was heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 120° C. for 30 min. After cooling, the reaction was acidified with 1 M hydrochloric acid and concentrated slightly on a rotary evaporator. The precipitate formed was filtered off, washed with water and dried under high vacuum. This gave 96 mg (94% pure, 57% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated slightly on a rotary evaporator
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-6a05ce0be6d34951be53edc4c35826aa
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

Loading…