Hydrochloric Acid → (5-Cyano-1-benzofuran-2-yl)boronic acid

HRID 1897821노트

반응식

HRID 1897821 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C.Cl>C1COCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][C:2]([B:17]([OH:20])[OH:18])=[CH:3][C:4]=2[CH:9]=1)#[N:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 27951841-Benzofuran-5-carbonitrileHCID 178418339Butyllithium

생성물 1

HCID 66787891(5-Cyano-1-benzofuran-2-yl)boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To benzofuran-5-carbonitrile (500 mg, 3.49 mmol) in THF (9.98 mL) at −78° C. was added nBuLi 1.6M in hexanes (2.401 mL, 3.84 mmol) dropwise. The mixture was stirred for 30 min at this temperature, and then trimethyl borate (0.858 mL, 7.68 mmol) was added dropwise. The mixture was stirred for 20 min, and then HCl 2N (11.52 mL, 23.05 mmol) was added. The bath was removed, and stirring continued for 30 min. The mixture was diluted with water and extracted with EtOAc three times, dried over magnesium sulfate, filtered, concentrated. Crude 5-cyanobenzofuran-2-ylboronic acid (623 mg, 87%) was then dried and used as is for the next step.

후처리

  1. stirringThe mixture was stirred for 20 min
  2. customThe bath was removed
  3. stirringstirring
  4. waitcontinued for 30 min
  5. additionThe mixture was diluted with water
  6. extractionextracted with EtOAc three times
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dry with materialCrude 5-cyanobenzofuran-2-ylboronic acid (623 mg, 87%) was then dried

출처 및 근거

ORD 기록
ord-feb9a316b97d462a8251d960475de7ab
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519142B2

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