Sodium Carbonate → 4'-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

HRID 900332ノート

反応式

HRID 900332 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]3[O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=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>[CH:22]1[C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][C:24]=2[C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:6]3[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)=[CH:18][CH:17]=2)=[CH:20][CH:21]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 590220984-(4-Bromophenyl)dibenzo[b,d]furan

生成物 1

HCID 596961794'-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4-(4-bromophenyl)-dibenzofuran (from the previous reaction) in toluene (40 mL). Tetrakis-(Triphenylphosphine)-palladium(0) (270 mg, 5 mol %) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100° 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 ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20% ethyl acetate in heptane) afforded the title compound has a white solid (1.51 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic extracts were washed with 0.5 N hydrochloric acid, water
  6. dry with materialdried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography (10-20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-fa8a76fc985649209197c262dabdddf6
出典データセット
uspto-grants-2008_04
特許番号
US07358248B2

反応ノート

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