Bromide ion → HCID 58062871, compound

HRID 659210Notes

Reaction equation

HRID 659210 reaction equation
CO[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=1.[Br-].[CH2:21]1[CH2:25]OC[CH2:22]1>>[CH:21]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=1)([CH3:25])[CH3:22]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028Tetrahydrofuran2×HCID 594385352-(2-Methoxy-4-trifluoromethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole

Product 1

HCID 58062871HCID 58062871, compoundYield 91%

Procedure

To a cooled (0° C.) solution of 2-(2-methoxy-4-trifluoromethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (intermediate AG) (1.0 g, 3.66 mmol) in 6.0 ml THF, was added dropwise a 1M ispropylmagnesium bromide solution in THF (11.0 ml, 10.98 mmol) maintaining the temperature below 5° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was cooled in an ice bath and quenched dropwise with 25 ml saturated NH4Cl solution. Ethyl acetate was added. The organic layer was separated and the aqueous layer was reextracted once with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified on silica gel (eluent: heptane/ethyl acetate 0 to 20%) to provide 0.95 g (91%) of the title compound as a light yellow oil. MS (m/e): 286.1 (M+H).

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. temperatureThe mixture was cooled in an ice bath
  3. customquenched dropwise with 25 ml saturated NH4Cl solution
  4. additionEthyl acetate was added
  5. customThe organic layer was separated
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude oil was purified on silica gel (eluent: heptane/ethyl acetate 0 to 20%)

Sources & evidence

ORD record
ord-574aff2c60b84806b2eebea3531ecc32
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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