Ammonium Chloride → 2-Methoxy-5-methyl-2'-(propan-2-yl)-1,1'-biphenyl

HRID 733021

反応式

HRID 733021 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)([CH3:13])[CH3:12].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.C(COC)OC.O>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:11]([CH3:13])[CH3:12])[CH:7]=1

参加物

10

反応物 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 891432-Bromo-4-methylanisoleHCID 27734772-Isopropylbenzeneboronic acid

生成物 1

HCID 687433682-Methoxy-5-methyl-2'-(propan-2-yl)-1,1'-biphenyl収率 118.7%

試薬・触媒・溶媒 5

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixed solution of 1 mL of water and 4 mL of dimethoxyethane was added into a flask into which 2-bromo-4-methylanisole (600 mg, 2.98 mmol), 2-isopropylphenylboronic acid (734 mg, 4.47 mmol), palladium acetate (16 mg, 0.074 mmol), triphenylphosphine (72 mg, 0.27 mmol), and potassium phosphate (1.12 g, 5.28 mmol) were already added, and then refluxed at normal temperature for 6 hours. After cooling to normal temperature, an ammonium chloride aqueous solution (5 mL) and 10 mL of diethylether were added thereto to separate an organic layer and extract residues with diethylether. The separated organic layer was dried with magnesium sulfate and volatile materials were removed to produce 850 mg of grey 4-methyl-2-(2′-isopropylphenyl)anisole solid. The anisole thus produced was dissolved in 5 mL of methylene chloride without separate purification, 3 mL of boron tribromide (1 M methylene chloride solution) was dropped thereonto at −78° C., and a reaction was carried out while the temperature slowly increased to normal temperature. After the reaction, a mixed solution of water (5 mL) and diethylether (10 mL) was added to separate an organic layer and extract an aqueous solution layer using diethylether (5 mL×3), and the separated organic layer was dried. Residues from which volatile components were removed at reduced pressure were purified using a silica gel chromatography tube in a mixed solvent of hexane and methylene chloride to produce 633 mg of white 4-methyl-2,6-(2′-isopropylphenyl)phenol solid.

後処理

  1. additionwere already added
  2. temperaturerefluxed at normal temperature for 6 hours
  3. temperatureAfter cooling to normal temperature
  4. customto separate an organic layer
  5. extractionextract residues with diethylether
  6. dry with materialThe separated organic layer was dried with magnesium sulfate and volatile materials
  7. customwere removed

出典と根拠

ORDレコード
ord-61952466d2cf4b238fbb8ea88bd4a825
出典データセット
uspto-grants-2009_09
特許番号
US07589042B2

関連ノート

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