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Sodium t-butoxide → HCID 59375006, 화합물

HRID 1811000
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HRID 1811000 반응식
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH2:17]Br)[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+]>C1COCC1.O>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH2:17][C:11]3[C:10](=[CH:15][C:14]([F:16])=[CH:13][CH:12]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 23676156Sodium t-butoxideHCID 66605334HCID 66605334, 화합물

생성물 1

HCID 59375006HCID 59375006, 화합물수율 58.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Step 3 A mixture of N-(3-bromo-2-methylphenyl)-2-(bromomethyl)-5-fluorobenzamide (2.54 g, 6.33 mmol) and sodium tert-butoxide (0.913 g, 9.50 mmol) in THF (80 mL) was stirred at rt for 30 min. The mixture was diluted with water and extracted with twice with DCM. The combined organic phases were washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-6-fluoroisoindolin-1-one as a white solid (1.18 g, 58%). 1H NMR (400 MHz, chloroform-d) δ 7.59-7.65 (2 H, m), 7.45-7.50 (1 H, m), 7.33 (1 H, td, J=8.6, 2.5 Hz), 7.19-7.24 (1 H, m), 7.15 (1 H, t, J=7.9 Hz), 4.68 (2 H, s), 2.31 (3 H, s). Mass spectrum m/z 320, 322 (M+H)+.

후처리

  1. extractionextracted with twice with DCM
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluting with hexane-EtOAc)

출처 및 근거

ORD 기록
ord-505241807ef94ac5a1f6870fa05fed8f
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362065B2

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