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

HRID 17285

反応式

HRID 17285 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 575758761-Fluoro-2-methoxy-5-methyl-3-nitrobenzene収率 73.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb51f80de4f3476789356b3d2878b0e3
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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