Hydrochloric Acid → [2-Ethyl-5-(trifluoromethyl)phenyl]boronic acid

HRID 924673노트

반응식

HRID 924673 반응식
C([Mg]Cl)(C)C.I[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[CH2:17][CH3:18].C[O:20][B:21](OC)[O:22]C.Cl>C1COCC1>[CH2:17]([C:8]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=1[B:21]([OH:22])[OH:20])[CH3:18]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 709807481-Ethyl-2-iodo-4-(trifluoromethyl)benzeneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 66571440[2-Ethyl-5-(trifluoromethyl)phenyl]boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

i-Propylmagnesium chloride (2M sol. in THF, 5.81 mL, 11.6 mmol) was added drop wise to a cooled (−30° C.) solution of 2-iodo-1-ethyl-4-(trifluoromethyl)benzene (3.48 g, 11.6 mmol) in dry THF (30 mL) and the reaction mixture was stirred at the same temperature for 30 min, under argon. After this time, trimethylborate (2.6 mL, 23.2 mmol) was added drop wise and the reaction mixture was stirred at the same temperature for 1.5 h. HCl (1 M, 10 mL) was added and the reaction mixture extracted with EtOAc (3×40 mL). The combined organic layers were dried over sodium sulfate and the solvent was evaporated to obtain the title compound as a white solid, crystallized from hexane (2.46 g, 97%).

후처리

  1. stirringthe reaction mixture was stirred at the same temperature for 1.5 h
  2. extractionthe reaction mixture extracted with EtOAc (3×40 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-324728e2e5fa46618cad2b61b0de3f9a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283224B2

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