Water → (2,6-Dicyanophenyl)boronic acid

HRID 24699

反応式

HRID 24699 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)#[N:2].[Li+].CC([N-]C(C)C)C.[B:19](OC)([O:22]C)[O:20]C.O>C1COCC1.CC(O)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[B:19]([OH:22])[OH:20])#[N:2]

参加物

7

反応物 4

HCID 962WaterHCID 8470Trimethyl borateHCID 12276IsophthalonitrileHCID 2724682Lithium diisopropylamide

生成物 1

HCID 22571817(2,6-Dicyanophenyl)boronic acid

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-96 °C

実験手順

1,3-Dicyanobenzene (1.00 g) was dissolved in freshly distilled THF (70 mL). This solution was cooled to −96° C. and LDA (4.2 mL of a 2M solution) was added dropwise to the cold solution under N2. The mixture was stirred for 30 min at −96° C. and (MeO)3B (1.3 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was taken up in CH2Cl2, filtered and evaporated to yield 2,6-dicyanobenzeneboronic acid (0.56 g).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. stirringthe resulting mixture was stirred for 0.5 h
  4. extractionextracted with EtOAc
  5. washThe organic layer was further washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-ee26bd4b04f6458fba5b11f5bfdac889
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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