Hydrochloric Acid → 3-bromo-4-fluoro-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 73728

반응식

HRID 73728 반응식
O=S(Cl)Cl.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([OH:11])=O.CCN(C(C)C)C(C)C.[F:25][C:26]([F:36])([F:35])[O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.Cl>C1(C)C=CC=CC=1.C1COCC1.CN(C=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([NH:32][C:31]1[CH:33]=[CH:34][C:28]([O:27][C:26]([F:25])([F:35])[F:36])=[CH:29][CH:30]=1)=[O:11]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 705093-Bromo-4-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)aniline

생성물 1

HCID 867025923-bromo-4-fluoro-N-(4-(trifluoromethoxy)phenyl)benzamide

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

SOCl2 (2.92 mL, 40.0 mmol) and DMF (0.5 mL) were added dropwise to a suspension of 3-bromo-4-fluorobenzoic acid (1.752 g, 8 mmol) in toluene (20 mL) and the RM was stirred at 80° C. for 1 h. The solvent was evaporated off under reduced pressure and the residue was diluted with THF (15 mL). DIPEA (2.79 mL, 16.00 mmol) was added and the mixture was cooled to 0° C., treated with a solution of 4-trifluoromethoxyaniline (1.181 mL, 8.80 mmol) in THF (5 mL) and stirred for 1 h. The RM was treated with aq. 1 M HCl (50 mL), and extracted with TBME. The combined extracts were washed with aq. 1 M HCl, aq. 1 M NaOH and brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to give a residue was crystallized from n-heptane/DCM to afford the title compound as a white solid. UPLC-MS (Condition 1) tR=3.18 min, m/z=377.9/379.9 [M+H]+, m/z=375.9/377.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.38 (d, J=8.6 Hz, 2H) 7.56 (t, J=8.7 Hz, 1H) 7.87 (d, J=9.0 Hz, 2H) 8.00-8.06 (m, 1H) 8.32 (dd, J=6.6, 2.2 Hz, 1H) 10.50 (s, 1H).

후처리

  1. customThe solvent was evaporated off under reduced pressure
  2. additionthe residue was diluted with THF (15 mL)
  3. temperaturethe mixture was cooled to 0° C.
  4. stirringstirred for 1 h
  5. extractionextracted with TBME
  6. washThe combined extracts were washed with aq. 1 M HCl, aq. 1 M NaOH and brine
  7. dry with materialdried over MgSO4
  8. customthe solvent was evaporated off under reduced pressure
  9. customto give a residue
  10. customwas crystallized from n-heptane/DCM

출처 및 근거

ORD 기록
ord-51c7ea58deb7442f8c6708ba79a2a7e2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829195B2

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