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Dichloromethane → Methyl 3-ethoxy-2'-fluorobiphenyl-4-carboxylate

HRID 531118
ノート
印刷プレビュー

反応式

HRID 531118 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[F-].[Cs+].ClCCl.[CH2:16]([O:18][C:19]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:17]>O.COCCOC>[CH2:16]([O:18][C:19]1[CH:28]=[C:27]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:17]
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 6344DichloromethaneHCID 25953Cesium fluorideHCID 27343542-Fluorophenylboronic acidHCID 66635397Methyl 2-ethoxy-4-iodobenzoate

生成物 1

HCID 90423758Methyl 3-ethoxy-2'-fluorobiphenyl-4-carboxylate収率 95.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

(2-Fluorophenyl)boronic acid (0.918 g), cesium fluoride (1.99 g), and a dichloromethane adduct of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.714 g) were added to a mixture of methyl 2-ethoxy-4-iodobenzoate (1.34 g) and DME (20 mL), and the resultant mixture was stirred at 100° C. for 15 hours in an argon atmosphere. Water was added to the reaction mixture, and the mixture was filtered through celite. The filtrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.15 g).

後処理

  1. filtrationthe mixture was filtered through celite
  2. extractionThe filtrate was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off 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-64e55e28ac84454e8ed8595e3c616473
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09353108B2

反応ノート

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