Methanol → Methyl 2-chloro-4-methylbenzoate

HRID 351120

반응식

HRID 351120 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([CH:51]=[O:52])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:46]([O:52][CH3:51])=[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 DMF (25 mL) is added Pd(OAc)2 (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. After cooling H2O (50 mL) is added. The mixture is extracted with hexanes (2×50 mL). The combined organic layers are dried over Na2SO4, filtered, concentrated and chromatographed with 0–3% EtOAc in hexanes. 1.24 g (28%) of methyl 2-chloro-4-methylbenzoate is isolated as a colorless oil. EIMS m/e 184 (M+; 35Cl) and 186 (M+; 37Cl).

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. temperatureAfter cooling H2O (50 mL)
  6. additionis added
  7. extractionThe mixture is extracted with hexanes (2×50 mL)
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customchromatographed with 0–3% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-722eefee9f754a47a0574d530b790364
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183320B2

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