Chloromethyl Methyl Ether → HCID 10762778, compound

HRID 1669410Notes

Reaction equation

HRID 1669410 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([OH:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22][O:23][CH2:24]Cl>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([O:19][CH2:22][O:23][CH3:24])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 21914298HCID 21914298, compound

Product 1

HCID 10762778HCID 10762778, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-3-hydroxyphenyl 4-methylbenzenesulfonate in dry DMF (1.0 M) was treated with NaH (1.2 eq of a 60% dispersion in mineral oil) and the mixture was stirred at RT for 30 min. Chloromethyl methyl ether (1.2 eq) was then added dropwise and the mixture was stirred at RT overnight. The mixture was diluted with EtOAc and the organic phase washed with 1 N HCl and brine before drying (Na2SO4), filtering and concentrating in vacuo. The crude was purified by FC (PE/EtOAc 1/9) to afford the title compound (77%). (ES+) m/z 387, 389 (M+H)+.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. washthe organic phase washed with 1 N HCl and brine
  3. dry with materialbefore drying (Na2SO4)
  4. filtrationfiltering
  5. concentrationconcentrating in vacuo
  6. customThe crude was purified by FC (PE/EtOAc 1/9)

Sources & evidence

ORD record
ord-0aad44fd3554430b8d08d0a0f579526d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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