Potassium Carbonate → 1-Fluoro-2-methoxy-5-methyl-3-nitrobenzene

HRID 17285

반응식

HRID 17285 반응식
[C:1](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.Br[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([O:26][CH3:27])=[C:19]([F:28])[CH:18]=1.O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:28][C:19]1[CH:18]=[C:17]([CH3:1])[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]=1[O:26][CH3:27]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 5571594-Bromo-2-fluoro-6-nitroanisoleHCID 574072TrimethylboroxineHCID 86585896Sodium bicarbonate water

생성물 1

HCID 575758761-Fluoro-2-methoxy-5-methyl-3-nitrobenzene수율 73.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Under nitrogen atmosphere, potassium carbonate (218 mg, 1.58 mmol), tetrakistriphenylphosphine palladium(0) (58 mg, 50 μmol), trimethylboroxine (77 μl, 0.55 mmol) were added to a 1,4-dioxane (5 ml) solution of 4-bromo-2-fluoro-6-nitroanisole (125 mg, 0.5 mmol), followed by stirring with heating under reflux for 1 hour and a half. After cooling to room temperature, saturated sodium bicarbonate water was added to the reaction liquid, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (20:1) was concentrated under reduced pressure to obtain the entitled compound (68 mg, 70%) as an orange oily substance.

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hour
  3. extractionfollowed by extraction three times with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. concentrationthe eluate with n-hexane:ethyl acetate (20:1) was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fb51f80de4f3476789356b3d2878b0e3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

연결된 노트

불러오는 중…