Water → (4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester

HRID 1754961노트

반응식

HRID 1754961 반응식
[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1I.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C(N(CC)CC)C.O>C1COCC1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57543475Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamate

생성물 1

HCID 66816224(4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester수율 98.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

(4-Bromo-2-iodo-5-methyl-phenyl)-carbamic acid methyl ester (605 mg, 1.64 mmol) was dissolved in THF (6 ml). (Trimethylsilyl)acetylene (0.70 ml, 4.95 mmol), copper iodide (33.5 mg, 0.175 mmol), Pd(PPh3)2Cl2 (56.5 mg, 0.081 mmol) and triethylamine (0.690 ml, 4.95 mmol) were added and the mixture was stirred at room temperature for four hours. Water was added to the reaction system, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to give (4-bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester (548 mg, 98%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-771d5be57ea242c48f04c7a35d2f0c28
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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