Sodium Carbonate → HCID 10620805, 화합물

HRID 343253노트

반응식

HRID 343253 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1B(O)O.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:3]2[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:7]([F:8])[C:2]=2[F:1])=[CH:24][CH:23]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzene2회HCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acid

생성물 1

HCID 10620805HCID 10620805, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

A solution of 2,3-difluro-4-octoxyphenylboronic acid (5) (8.29 g, 0.029 mol) in dimethoxyethane (40 ml) was added to a solution of 4-bromoiodobenzene (6.80 g, 0.024 mol) and tetrakis(triphenylphosphine)palladium (0) (1.4 8 g. 1.29 mmol) in dimethoxyethane (40 ml) under nitrogen. To this, 2M sodium carbonate (60 ml) was added. The stirred mixture was refluxed gently. Progress of the reaction was carefully monitored using tic until the 4-bromoiodobenzene had reacted completely (usually 4-5hr). The layers were separated and the aqueous layer once more extracted with ether. The combined organic layers were washed with brine and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1) to give a white solid which was recrystallised from pentane (-20° C.) to yield colourless crystals.

후처리

  1. temperatureThe stirred mixture was refluxed gently
  2. customhad reacted completely (usually 4-5hr)
  3. customThe layers were separated
  4. extractionthe aqueous layer once more extracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1)
  9. customto give a white solid which
  10. customwas recrystallised from pentane (-20° C.)
  11. customto yield colourless crystals

출처 및 근거

ORD 기록
ord-66e3316ba47240538a7c235187b81555
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861109

반응 노트

불러오는 중…