Water → 2,6-Dichlorobenzeneboronic acid

HRID 24698

反応式

HRID 24698 の反応式
Br[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:9].[Li]CCCC.[B:15](OC)([O:18]C)[O:16]C.O>C1COCC1.CCCCCC.CC(O)=O>[Cl:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[B:15]([OH:18])[OH:16]

参加物

8

反応物 4

HCID 962WaterHCID 8470Trimethyl borateHCID 295681-Bromo-2,6-dichlorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 27343322,6-Dichlorobenzeneboronic acid

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

1-Bromo-2,6-dichlorobenzene (2.00 g) was dissolved in freshly distilled THF (7 mL). This solution was cooled to −78° C. and n-BuLi (8.3 mL of a 1.6M solution in hexane) was added dropwise to the cold solution under N2. The mixture was stirred for 5 min at −78° C. and (MeO)3B (2.2 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 to yield 2,6-dichlorobenzeneboronic acid (1.6 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

出典と根拠

ORDレコード
ord-4c5b70b56b314212ba05587c2efe66d4
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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