Bromide ion → HCID 58136965, compound

HRID 657967Notes

Reaction equation

HRID 657967 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1.Br[CH2:18][CH:19]([O:21][CH3:22])C.[H-].[Na+].[Br-]>CN(C=O)C.CC(=O)OCC>[CH3:22][O:21][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:9])([F:10])([F:11])[F:12])[CH:7]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 24758Sodium hydrideHCID 52402123465-33-0HCID 58136805HCID 58136805, compound

Product 1

HCID 58136965HCID 58136965, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-[3-Hydroxy-5-(pentafluorosulfanyl)phenyl]ethanone (O3.050; 700 mg) and 1-bromo-2-methoxypropane (490 mg) were dissolved in DMF (10 ml), and sodium hydride (77 mg) was added. After stirring at RT for 2 h, further bromide (100 μl) was added and the mixture was heated to 50° C. for 6 h. Then the DMF was drawn off and the residue was taken up in EA, washed with water, dried, filtered and concentrated. 670 mg of the title compound were obtained. LC-MS rt: 1.71 min [M+H]+: 335.1 (met. a)

Workup

  1. temperaturethe mixture was heated to 50° C. for 6 h
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69ffbb5b4dc845cd9a1138cb14eaf89f
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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