Sodium Hydroxide → 1-(2,6-Dimethoxyphenyl)naphthalene

HRID 54027

반응식

HRID 54027 반응식
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[C:12]1(OB(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]1([C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=2[O:10][CH3:11])[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 6122962-Bromo-1,3-dimethoxybenzeneHCID 13862914Naphthylboric acid

생성물 1

HCID 154981511-(2,6-Dimethoxyphenyl)naphthalene수율 78.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1-bromo-2,6-dimethoxybenzene, (2.63 g, 12.1 mmol), tetrakis(triphenylphosphine)palladium (0) (0.91 g, 0.76 mol) and 1-naphthylboric acid (4.16 g, 23.9 mmol) in 1,4-dioxane (160 ml), a 2N aqueous solution of sodium hydroxide (13 ml) was added, and the mixture was heated to reflux. After cooling, the solvent was evaporated off, and the residue was dissolved in diethyl ether. The diethyl ether solution was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated off, and the residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1) to obtain 1-naphthyl-2,6-dimethoxybenzene (2.50 g).

후처리

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated off
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe diethyl ether solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated off
  8. customthe residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-0aae8bddb0dc42ebbc926bf057bf5887
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621129

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