Bromine → HCID 57567188, compound

HRID 1445951Notes

Reaction equation

HRID 1445951 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])[CH:3]1[O:7][C:6](=[O:8])[CH:5]=[C:4]1[O:9][CH3:10].[Br:21]Br>C(#N)C>[Br:21][C:5]1[C:6](=[O:8])[O:7]/[C:3](=[CH:2]\[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])/[C:4]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 13987268HCID 13987268, compound

Product 1

HCID 57567188HCID 57567188, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-{hydroxy-[2-(trifluoromethyl)phenyl]methyl}-4-methoxy-5H-furan-2-one (2.9 g, 10.1 mmol) in acetonitrile at room temperature is treated dropwise with bromine (0.52 ml, 10.1 mmol), stirred for 24 h and concentrated in vacuo. The resultant residue is diluted with CH2Cl2 and triethylamine (4.25 ml), cooled in an ice bath, treated with methane sulfonyl chloride (1.6 ml), stirred for 0.5 h at ice bath temperatures, allowed to warm to room temperature for 2 h and diluted with EtOAc and water. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. This residue is flash chromatographed (SiO2, hexane/EtOAc as eluent) to afford the title product as a white solid, 0.20 g (6% yield), mp 136-138° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resultant residue is diluted with CH2Cl2 and triethylamine (4.25 ml)
  3. temperaturecooled in an ice bath
  4. additiontreated with methane sulfonyl chloride (1.6 ml)
  5. stirringstirred for 0.5 h at ice bath temperatures
  6. additiondiluted with EtOAc and water
  7. customThe organic phase is separated
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customchromatographed (SiO2, hexane/EtOAc as eluent)

Sources & evidence

ORD record
ord-d9356142d7464b668e231a10daf08b1e
Source dataset
uspto-grants-2010_02
Patent number
US07666904B2

Reaction notes

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