Hydrochloric Acid → 4-Bromo-2-isopropylphenyl methanesulfonate

HRID 2243516Notes

Reaction equation

HRID 2243516 reaction equation
F[C:2](F)(F)[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Br:16][C:17]1[CH:22]=[CH:21][C:20](O)=[C:19]([CH:24]([CH3:26])[CH3:25])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:2][S:3]([O:6][C:20]1[CH:21]=[CH:22][C:17]([Br:16])=[CH:18][C:19]=1[CH:24]([CH3:26])[CH3:25])(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 147934824-Bromo-2-(propan-2-yl)phenol

Product 1

HCID 230907374-Bromo-2-isopropylphenyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.47 mL) was added to an ice-cooled mixture of 4-bromo-2-isopropylphenol (0.5 g) and pyridine (0.28 mL) in methylene chloride (5 mL) with stirring. The mixture was stirred for 10 min, and poured into a mixture of ethyl acetate and 1 mol/L hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/10) to afford 4-bromo-2-isopropylphenyl methanesulfonate (0.71 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred for 10 min
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/10)

Sources & evidence

ORD record
ord-139b248353e44c4cb951a506a2296fcb
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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