Potassium Carbonate → HCID 84769512、化合物

HRID 1748732ノート

反応式

HRID 1748732 の反応式
Br[C:2]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:13]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Cl:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([CH3:13])[CH:9]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 574072Trimethylboroxine2 回HCID 848037721616359-84-2

生成物 1

HCID 84769512HCID 84769512、化合物収率 81%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a degassed solution of 2-bromo-4-chloro-5-methoxybenzaldehyde (1.46 g, 5.9 mmol) and trimethylboroxine (0.82 mL, 5.9 mmol) in 1,4-dioxane (80 mL) was added potassium carbonate (2.43 g, 17.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.68 g, 0.6 mmol). The mixture was heated under reflux for about 23 h, then more tetrakis(triphenylphosphine)palladium(0) (0.17 g, 0.15 mmol) and trimethylboroxine (0.2 mL, 1.4 mmol) were added and the mixture was heated under reflux for about another 8 h. After cooling to rt the mixture was filtered over diatomaceous earth and concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:6) to give 4-chloro-5-methoxy-2-methylbenzaldehyde (0.87 g, 4.7 mmol, 81%) as a pale yellow solid: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.60 (3 H, s); 3.95 (3 H, s); 7.29 (1 H, s); 7.37 (1 H, s); 10.3 (1 H, s).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for about 23 h
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for about another 8 h
  5. filtrationwas filtered over diatomaceous earth
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:6)

出典と根拠

ORDレコード
ord-fda3b95226a148ebbf5d846d4b671adf
出典データセット
uspto-grants-2015_10
特許番号
US09150592B2

反応ノート

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