Sodium Carbonate → 2-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene

HRID 470730노트

반응식

HRID 470730 반응식
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1B(O)O)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:23]1[CH:22]=[C:21]([Br:24])[CH:20]=[CH:19][C:18]=1[F:17])[CH3:2]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 16213801(2-Ethoxynaphthalen-1-yl)boronic acid

생성물 1

HCID 677732662-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene수율 70%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In the atmosphere of argon, 22.7 g of 2-ethoxynaphthalene-1-boronic acid, 30.0 g of 2-fluoro-5-bromoiodobenzene, 2.31 g of tetrakistriphenylphosphine palladium (0), 300 mL of toluene and 150 mL of an aqueous 2M solution of sodium carbonate were placed in a flask, and the resulting mixture was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and then, an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate, and concentrated. Residues were purified by means of silica gel column chromatography, whereby 24.1 g (yield: 70%) of 2-ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene was obtained.

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customResidues were purified by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-79f11602fefc49d3af2c3c718ac9db72
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629430B2

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