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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydrochloric Acid → (3-Chloro-4-ethoxy-2-fluorophenyl)boronic acid

HRID 2099000
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HRID 2099000 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH3:11])=[C:5]([Cl:12])[C:4]=1[F:13].[B:14](OC)([O:17]C)[O:15]C.Cl>C1COCC1.C(O)(=O)C>[Cl:12][C:5]1[C:4]([F:13])=[C:3]([B:14]([OH:17])[OH:15])[CH:8]=[CH:7][C:6]=1[O:9][CH2:10][CH3:11]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 5462224MagnesiumHCID 534149841-Bromo-3-chloro-4-ethoxy-2-fluorobenzene

생성물 1

HCID 51358177(3-Chloro-4-ethoxy-2-fluorophenyl)boronic acid수율 83.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 8028Tetrahydrofuran용매3회

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온도
50 °C

실험 절차

4.79 g of well dried magnesium and 50 mL of THF were added to a reactor in a nitrogen atmosphere and heated to 50° C. 50.0 g of the compound (C2) dissolved in 200 mL of THF was added dropwise thereto over 60 minutes in a temperature range of 43 to 48° C., followed by stirring for 60 minutes. The resulting reaction mixture was cooled to 25° C. Thereafter, the reaction mixture was added dropwise to a solution of 24.6 g of trimethyl borate and 100 mL of THF cooled to −50° C. over 60 minutes in a nitrogen atmosphere in a temperature range of −60 to −40° C. The reaction mixture was warmed to 0° C. and then poured into 400 mL of 3N hydrochloric acid at 0° C. 700 mL of acetic acid was added to the solution, followed by mixing, and the mixture was then left to rest to separate into an organic layer and an aqueous layer, followed by extracting. The resulting organic layer was collected and washed with a saturated sodium hydrogen carbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain a residue. The residue was recrystallized from heptane. The recrystallization operation was repeated to obtain 35.9 g of 3-chloro-4-ethoxy-2-fluorophenylboronic acid (b58). The resulting compound (b58) was a yellowish solid.

후처리

  1. additionwas added dropwise
  2. customThe resulting reaction mixture
  3. temperaturewas cooled to 25° C
  4. temperaturecooled to −50° C. over 60 minutes in a nitrogen atmosphere in a temperature range of −60 to −40° C
  5. temperatureThe reaction mixture was warmed to 0° C.
  6. additionby mixing
  7. waitthe mixture was then left
  8. customto separate into an organic layer
  9. extractionby extracting
  10. customThe resulting organic layer was collected
  11. washwashed with a saturated sodium hydrogen carbonate aqueous solution and water
  12. dry with materialby drying over anhydrous magnesium sulfate
  13. distillationThereafter, the solvent was distilled off under reduced pressure
  14. customto obtain a residue
  15. customThe residue was recrystallized from heptane

출처 및 근거

ORD 기록
ord-b4f0d495b4b545bd8d36ae929ecd3d6e
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07569258B2

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