Hydrochloric Acid → 5-Bromo-2-(2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde

HRID 225442노트

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HRID 225442 반응식
[Br:1][C:2]1[C:3]([F:12])=[C:4]([F:11])[C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].C(N(CC)CC)C.[CH3:20][C@H:21]1[O:26][C@H:25]([CH3:27])[CH2:24][NH:23][CH2:22]1.Cl>C(#N)C>[Br:1][C:2]1[C:3]([F:12])=[C:4]([F:11])[C:5]([N:23]2[CH2:22][CH:21]([CH3:20])[O:26][CH:25]([CH3:27])[CH2:24]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11137133trans-2,6-DimethylmorpholineHCID 735543605-Bromo-2,3,4-trifluorobenzaldehyde

생성물 1

HCID 866145005-Bromo-2-(2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde수율 90.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

5-Bromo-2,3,4-trifluoro-benzaldehyde (10 g, 41.8 mmol) was dissolved in dry acetonitrile (70 mL). Triethylamine (6.4 mL, 46.0 mmol) was added, followed by trans-2,6-dimethylmorpholine (BASF, 5.3 g, 46 mmol). The mixture was refluxed for 24 hours, then cooled to room temperature, and treated with 1N HCl (58 mL). The acetonitrile was removed by rotoevaporation and the resulting solids were filtered, washed with water then dissolved in THF (100 mL). The solution was dried over MgSO4 and concentrated to a yellow oil. Hexanes were added and the mixture was re-concentrated to give 12.66 g of a yellow powder. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.26 (d, J=6.4 Hz, 6H), 2.92 (m, 2H), 3.28 (d, J=11.7 Hz, 2H), 4.15 (m, 2H), 7.78 (dd, J=7.2, 2.3 Hz, 2H), 10.32 (s, 4H).

후처리

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe acetonitrile was removed by rotoevaporation
  3. filtrationthe resulting solids were filtered
  4. washwashed with water
  5. dissolutionthen dissolved in THF (100 mL)
  6. dry with materialThe solution was dried over MgSO4
  7. concentrationconcentrated to a yellow oil
  8. additionHexanes were added
  9. concentrationthe mixture was re-concentrated

출처 및 근거

ORD 기록
ord-fb0a9a8173744647bff275131bc563e3
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557100B2

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