Methanol → Methyl 2-chloro-4-methylbenzoate

HRID 6969

反応式

HRID 6969 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[Cl:9].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:46][OH:47].CN(C)[CH:50]=[O:51]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:46]([O:51][CH3:50])=[O:47]

参加物

7

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 1387894-Bromo-3-chlorotoluene

生成物 1

HCID 22019481Methyl 2-chloro-4-methylbenzoate収率 28%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
80 °C

実験手順

To 4-bromo-3-chlorotoluene (4.97 g, 24.2 mmol) in dimethylformamide (25 mL) is added palladium acetate (0.54 g, 2.42 mmol), 1,3-bis(diphenylphosphino)propane (0.998 g, 2.42 mmol), triethylamine (12.5 mL) and methanol (12.5 mL). The reaction vessel is evacuated and purged three times with carbon monoxide gas. A balloon filled with carbon monoxide gas is used to maintain the carbon monoxide atmosphere. The reaction mixture is heated at 80° C. for 8 hr. The mixture is washed with water and extracted with hexanes (2×50 mL). The combined organic layers are dried over sodium sulfate, filtered, concentrated, and chromatographed with 0–3% ethyl acetate in hexanes. 1.24 g (28%) of methyl 2-chloro-4-methylbenzoate is isolated as a colorless oil.

後処理

  1. customThe reaction vessel is evacuated
  2. custompurged three times with carbon monoxide gas
  3. additionA balloon filled with carbon monoxide gas
  4. temperatureto maintain the carbon monoxide atmosphere
  5. washThe mixture is washed with water
  6. extractionextracted with hexanes (2×50 mL)
  7. dry with materialThe combined organic layers are dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed with 0–3% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-aee51196cc95496697f04b34ba5c4da1
出典データセット
uspto-grants-2006_08
特許番号
US07084170B2

関連ノート

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