Sodium Carbonate → 4-(4-Bromophenyl)dibenzo[b,d]furan

HRID 900331노트

반응식

HRID 900331 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)=[CH:20][CH:19]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 2734328Dibenzofuran-4-boronic acid

생성물 1

HCID 590220984-(4-Bromophenyl)dibenzo[b,d]furan

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 mL) was added to a stirred solution of 1-bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (271 mg, 5 mol %) in toluene (40 mL). 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90° C. (oil bath temp.) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2×20 mL). The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MgSO4, filtered and concentrated in vacuo to yield 4-(4-bromophenyl)-dibenzofuran as a yellow solid, which was used immediately without further purification.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and diethyl ether
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with diethyl ether (2×20 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialThe ethereal solution was dried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c725ac4a80e64d79853d3d1b1801eba1
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358248B2

반응 노트

불러오는 중…