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3-Nitrophenylboronic Acid → 3-(4-Ethoxypyridin-2-yl)nitrobenzene

HRID 1059932
ノート
印刷プレビュー

反応式

HRID 1059932 の反応式
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[N+:11]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:18]2[CH:19]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=[CH:16][CH:17]=2)[CH:7]=1)[CH3:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 5651602-Bromo-4-ethoxypyridine

生成物 1

HCID 186675793-(4-Ethoxypyridin-2-yl)nitrobenzene収率 83.5%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 8071
1,2-Dimethoxyethane
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 2-bromo-4-ethoxypyridine (879 mg), 3-nitrophenylboronic acid (944 mg) and tetrakis(triphenylphosphine)-palladium (251 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (5.66 ml). The mixture was stirred at 90° C. for 8 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 40 g, 25% ethyl acetate in n-hexane) to give 3-(4-ethoxypyridin-2-yl)nitrobenzene (887 mg).

後処理

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 40 g, 25% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-7d342f939d5145d6b4c469e0fb552f81
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06521643B1

反応ノート

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