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4-(Methylthio)phenylboronic acid → HCID 23450971、化合物

HRID 1598826
ノート
印刷プレビュー

反応式

HRID 1598826 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[CH3:15][S:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+].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>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:20]2[CH:21]=[CH:22][C:17]([S:16][CH3:15])=[CH:18][CH:19]=2)=[CH:9][CH:10]=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 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 132706302-Bromo-4'-fluoro-1,1'-biphenyl

生成物 1

HCID 23450971HCID 23450971、化合物収率 93.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140
Toluene
溶媒
HCID 10340Sodium Carbonate溶媒

実験手順

Under nitrogen, 200 mg of Pd(PPh3)4 was added to a stirred solution of 500 mg (2.0 mmol) of 1-bromo-2-(4-fluorophenyl)benzene (Step 1) and 500 mg (3.0 mmol) of 4-methylthiophenylboronic acid (Step 2) in 7 mL of toluene, 7 mL of ethanol and 7 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The resulting solution was washed with water and dried over MgSO4. Purification by silica gel chromatography (Waters LC-2000) with ethyl acetate/hexane (2:98) as the eluent gave 550 mg of 1-(4-fluorophenyl)-2-[4-(methylthio)phenyl]benzene as a semi-solid: NMR (CDCl3) δ 2.46 (s, 3H), 6.92 (t, J=8 Hz, 2H), 7.02-7.14 (m, 6H) 7.37-7.42 (m, 4H). MS (EI): m/e (rel intensity) 294 (100), 279 (39), 277 (56), 246 (74), 227 (40), 190 (43) 190 (38), 140 (44).

後処理

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialdried over MgSO4
  6. customPurification by silica gel chromatography (Waters LC-2000) with ethyl acetate/hexane (2:98) as the eluent

出典と根拠

ORDレコード
ord-ba85dcf4781e4c20ab4a085efa3bbf0d
出典データセット
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05739166

反応ノート

読み込み中…

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