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

HRID 1755522ノート

反応式

HRID 1755522 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 111427014-Bromo-4',4''-dimethyltriphenylamine2 回HCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e8d9a463afab493ba04c46f319dad949
出典データセット
uspto-grants-2015_10
特許番号
US09172051B2

反応ノート

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