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

HRID 225442ノート

反応式

HRID 225442 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb0a9a8173744647bff275131bc563e3
出典データセット
uspto-grants-2009_07
特許番号
US07557100B2

反応ノート

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