Dimethylformamide → 2-Bromo-3-fluoro-6-nitroaniline

HRID 1056097노트

반응식

HRID 1056097 반응식
[Br:1][C:2]1[C:7](F)=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[F:12].C(=O)([O-])[O-].[NH4+].[NH4+].C[N:20](C=O)C.CCN(CC)CC>O>[Br:1][C:2]1[C:3]([F:12])=[CH:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH2:20]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 517111Ammonium CarbonateHCID 137327452-Bromo-1,3-difluoro-4-nitrobenzene

생성물 1

HCID 194297802-Bromo-3-fluoro-6-nitroaniline수율 97%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Prepared according to WO 2010/046388. 2-Bromo-1,3-difluoro-4-nitrobenzene (600a) (27.15 g, 114 mmol) was treated with ammonium carbonate (Sigma Aldrich, 10.96 g, 114 mmol) and DMF (200 mL) followed by Et3N (47.7 mL, 342 mmol) and stirred at RT for 48 h. The mixture was treated with water and extracted with DCM (300 mL). The DCM layer was washed with water (3×200 mL) and brine (3×200 mL), dried over MgSO4, filtered and concentrated affording crude 2-bromo-3-fluoro-6-nitroaniline (25.99 g, 111 mmol, 97% yield) as a bright yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.22 (1H, dd, J=9.6, 5.9 Hz), 6.81 (2H, br. s.), 6.56 (2H, dd, J=9.6, 7.2 Hz). 19F NMR (376 MHz, CDCl3) δ ppm −90.92 (1F, s). m/z (ESI, +ve ion) 234.9/236.9 (M+H)+.

후처리

  1. customPrepared
  2. extractionextracted with DCM (300 mL)
  3. washThe DCM layer was washed with water (3×200 mL) and brine (3×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3c5dabb38be2424597224e6292c334db
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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