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Ethyl Acetate → Methyl 2-(2-benzyloxy-4-fluorophenyl)-3-methyl-5-nitrobenzoate

HRID 909302
ノート
印刷プレビュー

反応式

HRID 909302 の反応式
[CH3:1][C:2]1[C:3](OS(C(F)(F)F)(=O)=O)=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:23]([O:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1B(O)O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:23]([O:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[C:3]1[C:2]([CH3:1])=[CH:11][C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27826652-Benzyloxy-4-fluorophenylboronic acidHCID 58026836Methyl 3-methyl-5-nitro-2-trifluoromethylsulfonyloxybenzoate

生成物 1

HCID 58026740Methyl 2-(2-benzyloxy-4-fluorophenyl)-3-methyl-5-nitrobenzoate収率 70%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of methyl 3-methyl-5-nitro-2-trifluoromethylsulfonyloxybenzoate (Reference Compound No. 1-4-(3), 13.26 g, 38.6 mmol), 2-benzyloxy-4-fluorophenylboronic acid (14.3 g, 58.1 mmol), potassium phosphate (21.3 g, 100 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.23 g, 2.80 mmol) was suspended in anhydrous 1,4-dioxane (200 mL), and then the mixture was refluxed for 3 days. After cooling down, ethyl acetate (500 mL) was added thereto, and then the whole was washed with water (500 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (10.7 g) as a pale brown solid. (Yield 70%)

後処理

  1. temperaturethe mixture was refluxed for 3 days
  2. temperatureAfter cooling down
  3. washthe whole was washed with water (500 mL) and saturated brine (50 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-31c617d311e04edfa045c55c5c9ab6dd
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017775B2

反応ノート

読み込み中…

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