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Hydrochloric Acid → 1-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

HRID 1859396
ノート
印刷プレビュー

反応式

HRID 1859396 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([F:10])([F:9])[F:8])=[N:3]1.[Li+].CC([N-]C(C)C)C.C[O:20][B:21](OC)[O:22]C.Cl>C1COCC1>[CH3:1][N:2]1[C:6]([B:21]([OH:22])[OH:20])=[CH:5][C:4]([C:7]([F:10])([F:9])[F:8])=[N:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 2724682Lithium diisopropylamideHCID 27804041-Methyl-3-(trifluoromethyl)-1H-pyrazole

生成物 1

HCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
10 °C

実験手順

A solution of 1-methyl-3-trifluoromethylpyrazol (2 g) in 10 ml THF is cooled under an inert gas atmosphere to −78° C. A 2 M solution of LDA (9.75 ml) is added dropwise. The mixture is stirred to 10° C. for 1 h and cooled to −75° C. Trimethylborate (5.8 ml) is added and after stirring for 1 h at −75° C. the mixture is stirred overnight at ambient temperature. The resulting reaction solution is added to 10% hydrochloric acid (15 ml). The water phase is extracted 3 times with ethyl acetate and the combined organic phases are washed with water and a saturated sodium chloride solution. The organic phase is dried and evaporated and the residue is crystallized from water. After drying, one obtains the title compound as nearly colorless crystals (1.12 g) of mp. 138° C.

後処理

  1. temperaturecooled to −75° C
  2. stirringafter stirring for 1 h at −75° C. the mixture
  3. stirringis stirred overnight at ambient temperature
  4. customThe resulting reaction solution
  5. extractionThe water phase is extracted 3 times with ethyl acetate
  6. washthe combined organic phases are washed with water
  7. customThe organic phase is dried
  8. customevaporated
  9. customthe residue is crystallized from water
  10. customAfter drying

出典と根拠

ORDレコード
ord-b8b9c20b18d141b49324d4ebe17d2e8e
出典データセット
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06528456B2

反応ノート

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