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

HRID 2410481ノート

反応式

HRID 2410481 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].F[C:16]1[C:17](C)=[C:18]([C:22]2C=CC(C(O)=O)=C[C:23]=2COC)[CH:19]=[CH:20][CH:21]=1.C(C1C=CC=CC=1B(O)O)C.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>[CH2:22]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:16][C:17]=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])[CH3:23]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 580663983'-Fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

生成物 1

HCID 58554174Methyl 2'-ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylate収率 83%

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 (Intermediate 1 Step 2, 12.0 g, 46.3 mmol) in toluene (150 mL) and water (35 mL) under N2, was added 2-ethylbenzene boronic acid (9.02 g, 60.1 mmol) followed by potassium carbonate (19 g, 139 mmol) and Pd(PPh3)4 (2.67 g, 2.31 mmol). The reaction mixture was degassed with N2 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 sodium bicarbonate (100 mL), water (2×100 mL) and brine (100 mL). It was then dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, pet ether/EtOAc) to afford the title compound as a pale yellow liquid (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), 4.12-4.21 (2H, m), 3.94 (3H, s), 3.29 (3H, s), 2.28-2.43 (2H, m), 1.03 (3H, t).

後処理

  1. customThe reaction mixture was degassed with N2
  2. additionThe reaction mixture was diluted with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate (100 mL), water (2×100 mL) and brine (100 mL)
  4. dry with materialIt was then dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel, pet ether/EtOAc)

出典と根拠

ORDレコード
ord-d3f34a66e203473cbe81b7be6f14f4bd
出典データセット
uspto-grants-2014_08
特許番号
US08815919B2

反応ノート

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