Potassium Carbonate → Methyl 2'-ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 1630971ノート

反応式

HRID 1630971 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].[CH2:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH2:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14])[CH3:16]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate2 回

生成物 1

HCID 58554174Methyl 2'-ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylate収率 91.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate (12.0 g, 46.3 mmol, Intermediate A1 step 2) in toluene (150 mL) and water (35 mL) was added 2-ethyl benzene boronic acid (9.0 g, 60.1 mmol) followed by potassium carbonate (19.0 g, 139 mmol) and Pd(PPh3)4 (2.7 g, 2.3 mmol). The resulting mixture was degassed with N2 for 10 min and heated at 100° C. for 12 hours. The reaction mixture was diluted with EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, water (2×) and brine, and then dried (Na2SO4). The solvents were removed under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow oil (12.0 g, 83%). 1H NMR (CDCl3, 400 MHz) δ 8.25 (1H, s), 8.00 (1H, d), 7.35 (2H, m), 7.25 (2H, m), 7.08 (1H, d), 4.17 (2H, m), 3.94 (3H, s), 3.29 (3H, s), 2.43-2.28 (2H, m), 1.03 (3H, t).

後処理

  1. customThe resulting mixture was degassed with N2 for 10 min
  2. additionThe reaction mixture was diluted with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of NaHCO3, water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed under reduced pressure
  6. customThe residue was purified by chromatography (silica, pet ether/EtOAc)

出典と根拠

ORDレコード
ord-ec4946b04789425d91eb20954ab396a5
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

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