Hydrochloric Acid → 5-Bromo-2-methanesulfonylphenol

HRID 876219Notes

Reaction equation

HRID 876219 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4](F)[CH:3]=1.CS(CCO)(=O)=[O:15].[H-].[Na+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([OH:15])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 848342-(Methylsulfonyl)ethanolHCID 459337204-Bromo-2-fluoro-1-(methylsulfonyl)benzene

Product 1

HCID 702778455-Bromo-2-methanesulfonylphenolYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-bromo-2-fluoro-1-methylsulfonyl-benzene (2 g, 7.9 mmol) in DMF (15 mL) is added 2-methanesulfonyl-ethanol (1.47 g, 11.85 mmol). Sodium hydride (948.16 mg, 23.71 mmol) is added in portions at 0° C. The reaction mixture is allowed to come to r.t. and is added dropwise into cooled aq. hydrochloric acid. The aq. layer is extracted with ethyl acetate. The organic layer is dried over MgSO4, filtered and concentrated. The crude residue is purified by reversed phase HPLC. Yield 86%, m/z 251/253[M+H]+, rt 0.42 min, LC-MS Method X018_S01.

Workup

  1. customto come to r.t.
  2. additionis added dropwise
  3. extractionThe aq. layer is extracted with ethyl acetate
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue is purified by reversed phase HPLC
  8. customYield 86%, m/z 251/253[M+H]+, rt 0.42 min, LC-MS Method X018_S01

Sources & evidence

ORD record
ord-98aaed037df0448e8261e803329d67a9
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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