Hydrochloric Acid → HCID 68756870, compound

HRID 72987Notes

Reaction equation

HRID 72987 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6].[H-].[Na+].[CH3:17][OH:18].Cl>CCOC(C)=O.CN(C=O)C>[CH3:17][O:18][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24758Sodium hydrideHCID 265980733-Fluoro-4-(methylsulphonyl)benzoic acid

Product 1

HCID 68756870HCID 68756870, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 3-fluoro-4-methylsulfonyl-benzoic acid (490 mg, 2.25 mmol), sodium hydride (270 mg, 6.74 mmol), methanol (1.55 g, 2.0 mL, 48.3 mmol) was added DMF (5 mL) and reaction mixture was heated at 100° C. for 1 hour. The reaction mixture was cooled and diluted with EtOAc and acidified using 1 M HCl solution. The organic layer was separated, washed with saturated aqueous brine solution (3×), dried over sodium sulfate and concentrated in vacuo to give 3-methoxy-4-methylsulfonyl-benzoic acid (496 mg, 95%). ESI-MS m/z calc. 230.0. Found 231.3 (M+1)+; Retention time: 0.49 minutes (3 min run).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous brine solution (3×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e0e89dfa37c4c25bf90473eba05b4d6
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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