Benzo(B)Thiophene-2-Boronic Acid → 2-Phenylbenzo[b]thiophene

HRID 590956ノート

反応式

HRID 590956 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.O.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.[Pd]>[C:14]1([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 11575Iodobenzene

生成物 1

HCID 6108862-Phenylbenzo[b]thiophene収率 60%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of benzothiopheneboronic acid (1 g, 5.61 mmol) in ethanol (23 mL) was added to a mixture of iodobenzene (560 μL, 5 mmol), palladium tetrakis(triphenylphosphine) (460 mg, 0.4 mmol) and sodium carbonate (2.38 g, 22.4 mmol) in a mixture of toluene (15 mL) and water (15 mL). The reaction mixture was refluxed for 6 hours and then concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (10 mL). The biphasic mixture was acidified with an aqueous solution of hydrochloric acid 1N until pH 2. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the organic layer was washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (2a) as a yellow oil (640 mg, 3 mmol, 60%).

後処理

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (30 mL) and water (10 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  5. washthe organic layer was washed with water (10 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

出典と根拠

ORDレコード
ord-fe047421bd6045789e8b776bc33df7bb
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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