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

HRID 264599

반응식

HRID 264599 반응식
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.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>[CH2:32]([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]

참가 물질

8

반응물 4

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

생성물 1

HCID 214795504-(n-Pentoxyphenyl)-4'-carboxybiphenyl수율 70.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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) δ0.89 (t, 3H), 1.37 (m, 4H), 1.72 (m, 2H), 3.98 (t, 2H), 7.01 (d, 2H).

후처리

  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

출처 및 근거

ORD 기록
ord-0ab78d509caa495cabb27b4ae2337c97
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646245

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