Toluene → 1-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzene

HRID 591558노트

반응식

HRID 591558 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][SH:20])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.CCN(C(C)C)C(C)C>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].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.O>[F:10][C:4]1[CH:3]=[C:2]([S:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 804074-Methoxy-alpha-toluenethiolHCID 81531DiisopropylethylamineHCID 108220943-Bromo-5-fluoroanisole

생성물 1

HCID 897678621-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzene수율 91.4%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

실험 절차

To a mixture of 1-bromo-3-fluoro-5-methoxybenzene (5 g), (4-methoxyphenyl)methanethiol (3.76 g), and toluene (100 mL) were added Pd2(dba)3 (0.447 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.564 g) and DIPEA (8.52 mL). The mixture was stirred at room temperature overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (6.20 g).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-913009ee3728439fb3464c42344a6a54
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238639B2

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