Ethyl Acetate → 4-Tert-butoxy-3'-methoxybiphenyl

HRID 1600922ノート

反応式

HRID 1600922 の反応式
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+].O.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>[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

9

反応物 3

HCID 8857Ethyl AcetateHCID 169713-BromoanisoleHCID 113899354-tert-Butoxyphenylboronic acid

生成物 1

HCID 218306204-Tert-butoxy-3'-methoxybiphenyl収率 101.2%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 10340Sodium Carbonate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 4-tert-butoxybenzeneboronic acid (0.50 g), 3-bromoanisole (0.44 g), and tetrakis(triphenylphosphine)palladium(0) (0.09 g) in toluene (5 ml), ethanol(1.2 ml) and aqueous sodium carbonate (2 M, 2.4 ml) was heated at 100° C. for 19 hours. After cooling the reaction mixture was added to brine (50 ml) and ethyl acetate (50 ml). The organic layer was separated and dried over anhydrous magnesium sulfate. The solution was then filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:toluene 9:1 to give 4-tert-butoxy-3'-methoxybiphenyl (0.61 g). (MS (EI) 256 (M)+). Trifluoroacetic acid (5 ml) was added to a solution of 4-tert-butoxy-3'-methoxybiphenyl (0.60 g) in dichloromethane (20 ml) and the resulting solution stirred for 1 hour. The solution was then concentrated under reduced pressure. The residue was partitioned between a solution of saturated aqueous sodium hydrogen carbonate (25 ml) and ether (3×25 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane to give the sub-title compound as a solid (0.25 g).

後処理

  1. temperatureAfter cooling the reaction mixture
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with hexane:toluene 9:1

出典と根拠

ORDレコード
ord-3be9712fe08247379759ee4099e63928
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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