Trimethyl borate → (5-Cyano-2-Methoxyphenyl)Boronic Acid

HRID 2069905

반응식

HRID 2069905 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].C([Mg]Cl)(C)C.[B:17](OC)([O:20]C)[O:18]C>O1CCCC1>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([B:17]([OH:20])[OH:18])[CH:3]=1)#[N:6]

참가 물질

5

반응물 3

HCID 8470Trimethyl borateHCID 7360493-Bromo-4-methoxybenzonitrileHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic Acid수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

3-Bromo-4-methoxybenzonitrile (3.0 g, 14.2 mmol, 1.0 eq) was dissolved in anhydrous tetrahydrofuran (10 mLs). The solution cooled at −10° C. and stirred while isopropylmagnesium chloride (17.7 mmol, 8.8 mLs, 2.0 M in THF, 1.25 eq.) was added. The mixture was stirred for 1 hour and then trimethyl borate (1.87 g, 17.7 mmol, 2.0 mL) was added dropwise. The mixture was allowed to warm slowly to room temperature for 1 hour. The solvent was evaporated and the residue was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to a minimum volume under reduced pressure. The residue was recrystallized from hexanes to give 5-cyano-2-methoxybenzeneboronic acid (2.48 g, 99%) as a fluffy white powder.

후처리

  1. additionwas added
  2. temperatureto warm slowly to room temperature for 1 hour
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between 5% citric acid and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated to a minimum volume under reduced pressure
  9. customThe residue was recrystallized from hexanes

출처 및 근거

ORD 기록
ord-ec2add57e93f4fa7b8edc10c442a2f96
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299110B2

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