Water → 2-Fluoro-4-(3-trifluoromethylphenylthio)benzaldehyde

HRID 445422

反応式

HRID 445422 の反応式
C(N(C(C)C)C(C)C)C.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.Br[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[C:24]([F:30])[CH:23]=1.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:30][C:24]1[CH:23]=[C:22]([S:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:19])[F:20])[CH:13]=2)[CH:29]=[CH:28][C:25]=1[CH:26]=[O:27]

参加物

8

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1367513-(Trifluoromethyl)benzenethiolHCID 1435174-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 580226012-Fluoro-4-(3-trifluoromethylphenylthio)benzaldehyde収率 68%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 312751,4-Dioxane溶媒

実験手順

Under an argon atmosphere, ethyldiisopropylamine (7.0 mL), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (518 mg), xantphos (578 mg), and 3-trifluoromethylthiophenol (3.56 g) were added at room temperature into a solution of 4-bromo-2-fluorobenzaldehyde (4.06 g) in 1,4-dioxane (42 mL), and the resultant solution was heated to reflux for 5 hours. To the reaction solution added water, extracted with ethyl acetate, washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain the target product (4.08 g) as a colorless oil.

後処理

  1. temperatureto reflux for 5 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

出典と根拠

ORDレコード
ord-ba81324ddb7f4c3b85a8c5cb1aea8a62
出典データセット
uspto-grants-2013_07
特許番号
US08476305B2

関連ノート

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