Potassium Hydroxide → 2-(Benzyloxy)-3-fluorophenol

HRID 39016노트

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HRID 39016 반응식
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17]1CCOCC1.[OH-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 532169822-(Benzyloxy)-1-chloro-3-fluorobenzene

생성물 1

HCID 107751752-(Benzyloxy)-3-fluorophenol

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of 2-(benzyloxy)-1-chloro-3-fluorobenzene (3 g, 12.71 mmol), dioxane (6 ml), KOH (0.78 g, 14 mmol), water (6 ml), Tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol) and 2-di-tertbutylphosphine-2,4,6-triisopropylbiphenyl (0.22 g, 0.51 mmol) was flushed with N2 and heated under microwave radiation at 120° C. for 7 min. HCl (1 N) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.86 g). MS m/z (rel. intensity, 70 eV) 218 (M+, 4), 92 (8), 91 (bp), 65 (13), 51 (9).

후처리

  1. customwas flushed with N2
  2. additionHCl (1 N) was added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-9ab18781cc814d62921fc9a44e38d60c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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