Methanol → 1,4-Dibromo-2-methoxybenzene

HRID 2384928노트

반응식

HRID 2384928 반응식
C[C:2](C)([O-:4])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1F.CO>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1[O:4][CH3:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 1370041,4-Dibromo-2-fluorobenzeneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 133995571,4-Dibromo-2-methoxybenzene수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

Add dropwise potassium tert-butoxide (118.2 ml, 118.2 mmol, 1 M in hexane) to a solution of 1,4-dibromo-2-fluorobenzene (25.0 g, 98.5 mmol) in THF (492 mL) and MeOH (40 mL, 984.7 mmol) at RT. Heat the mixture at 70° C. overnight. Quench the mixture with water (50 mL), dilute with Et2O (400 mL), wash once with saturated NH4Cl (300 mL) and back extract the aqueous with Et2O (200 mL). Dry the combined organic phase over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% ethylacetate/hexane to give 22.0 g (84%) of the title compound. GC m/z (79Br81Br) 266 [M]+.

후처리

  1. customQuench the mixture with water (50 mL)
  2. additiondilute with Et2O (400 mL)
  3. washwash once with saturated NH4Cl (300 mL)
  4. extractionback extract the aqueous with Et2O (200 mL)
  5. dry with materialDry the combined organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatograph
  9. washeluting with 5-10% ethylacetate/hexane

출처 및 근거

ORD 기록
ord-4859eb24b11242a09b20888a638cf701
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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