Water → 2,6-Dichlorobenzeneboronic acid

HRID 24698

반응식

HRID 24698 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 27343322,6-Dichlorobenzeneboronic acid

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c5b70b56b314212ba05587c2efe66d4
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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