Hydrochloric Acid → 4-(n-Pentoxyphenyl)-4'-carboxybiphenyl

HRID 439701ノート

反応式

HRID 439701 の反応式
C(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)CCCC.I[C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1.[C:32](=[O:35])([O-])[O-].[Na+].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1>[CH2:32]([O:35][C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[CH:12][CH:11]=1)[CH2:12][CH2:7][CH2:8][CH3:9]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 120854-Iodobenzoic acidHCID 113580714'-Pentyloxybiphenyl-4-boronic Acid

生成物 1

HCID 214795504-(n-Pentoxyphenyl)-4'-carboxybiphenyl収率 70.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a stirred mixture of 4-(4-n-pentoxyphenyl)phenylboronic acid (1.0 g, 3.52 mmol) and 4-iodobenzoic acid (874 mg, 3.52 mmol) in ethanol (11 ml) and toluene (30 ml) was added an aqueous solution of sodium carbonate (2M, 5.3 ml, 10.6 mmol) followed by tetrakis-(triphenylphosphine)palladium (204 mg, 5 mol %). The reaction mixture was heated at 100° C. under a nitrogen atmosphere for a period of 18 h. The cooled mixture was acidified to pH 3 (1N HCl) and partitioned between ethyl acetate and water. The organic phase was washed with water (3×) and brine, dried with magnesium sulfate, and filtered through a bed of Celite. The solvent was removed in vacuo to give crude product which was purified by flash silica gel chromatography to provide 4-(n-pentoxyphenyl)-4'-carboxybiphenyl (450 mg): 1H NMR (400 MHz, DMSO-d6) δ 0.89 (t, 3), 1.37 (m, 4 ), 1.72 (m, 2), 3.98 (t, 2), 7.01 (d, 2).

後処理

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water (3×) and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered through a bed of Celite
  5. customThe solvent was removed in vacuo
  6. customto give crude product which
  7. customwas purified by flash silica gel chromatography

出典と根拠

ORDレコード
ord-c01487188bc3401eb539a27418771e4d
出典データセット
uspto-grants-1996_05
特許番号
US05516756

反応ノート

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