Methanol → Methyl 2-chloro-4-methylbenzoate

HRID 6969

반응식

HRID 6969 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 22019481Methyl 2-chloro-4-methylbenzoate수율 28%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aee51196cc95496697f04b34ba5c4da1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

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