Nitrogen → 2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2096395

반응식

HRID 2096395 반응식
[Zn](CC)[CH2:2]C.FC(F)(F)C(O)=O.N#N.C(I)I.[CH3:18][C:19]1([CH3:34])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=[CH2:33])[CH:27]=2)[O:20]1>C(Cl)Cl>[CH:32]1([C:28]2[CH:27]=[C:26]([B:21]3[O:20][C:19]([CH3:34])([CH3:18])[C:23]([CH3:24])([CH3:25])[O:22]3)[CH:31]=[CH:30][CH:29]=2)[CH2:2][CH2:33]1

참가 물질

7

반응물 5

HCID 947NitrogenHCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 222401702-(3-Ethenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 222402222-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane수율 10%

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

실험 절차

To a solution of Zn(C2H5)2 (1 M, 6 mL) in DCM (1 mL) was added trifluoro-acetic acid (0.46 ml, 6 mmol) in DCM (1 mL) very slowly under N2 in ice bath. The mixture was stirred for 20 minutes. CH2I2 (1.61 g, 6 mmol) in DCM (1 mL) was added to the mixture. After stirring for 20 minutes, 4,4,5,5-tetramethyl-2-(3-vinylphenyl)-1,3,2-dioxaborolane (690 mg, 3 mmol) in DCM (1 mL) was added. The mixture was stirred at room temperature for 2 hour. the mixture was quenched by NH4Cl solution, extracted with DCM 3 times, washed with brine, filtered and concentrated to give the residue, which was purified preparative TLC and HPLC to give 2-(3-cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (70 mg, 10%).

후처리

  1. stirringAfter stirring for 20 minutes
  2. stirringThe mixture was stirred at room temperature for 2 hour
  3. customthe mixture was quenched by NH4Cl solution
  4. extractionextracted with DCM 3 times
  5. washwashed with brine
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the residue, which
  9. customwas purified preparative TLC and HPLC

출처 및 근거

ORD 기록
ord-35b21563b998431697a124af13ebbb41
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450308B2

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