Hydrochloric Acid → [4-[Bis(4-methylphenyl)amino]phenyl]boronic acid

HRID 1755522노트

반응식

HRID 1755522 반응식
Br[C:2]1[CH:22]=[CH:21][C:5]([N:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Li]CCCC.[B:28](OC)([O:31]C)[O:29]C.Cl>C1COCC1>[C:10]1([CH3:13])[CH:11]=[CH:12][C:7]([N:6]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:5]2[CH:4]=[CH:3][C:2]([B:28]([OH:31])[OH:29])=[CH:22][CH:21]=2)=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 111427014-Bromo-4',4''-dimethyltriphenylamine2회HCID 178418339Butyllithium

생성물 1

HCID 23083792[4-[Bis(4-methylphenyl)amino]phenyl]boronic acid수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 4-bromo-N,N-di-p-tolylaniline (Compound 25) (12.55 g, 35.6 mmol) in anhydrous THF (100 mL), was added n-BuLi solution (16 mL, 2.5 M in hexanes) at −78° C. slowly. The resulting solution was stirred at −78° C. for about one hour. Then a freshly distilled trimethyl borate (B(OCH3)3) (5.6 mL) was added. The solution turned to yellow immediately, and was stirred at RT for about 2 hours. After addition of 1N HCl solution (150 mL), the whole was stirred at RT for about 18 hours and concentrated. The resulting solid was filtered and washed with diethyl ether to give a light yellow solid (Compound 26) (5.8 g, in 56% yield).

후처리

  1. stirringwas stirred at RT for about 2 hours
  2. stirringthe whole was stirred at RT for about 18 hours
  3. concentrationconcentrated
  4. filtrationThe resulting solid was filtered
  5. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-e8d9a463afab493ba04c46f319dad949
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09172051B2

반응 노트

불러오는 중…