Chloroform → HCID 73297273, Verbindung

HRID 333209

Reaktionsgleichung

Reaktionsgleichung von HRID 333209
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:8]1[O:16]C(C)(C)C(C)(C)[O:9]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.[Br:27][CH2:28][C:29](Br)=[O:30]>O.CCCCCC.C(OCC)(=O)C>[Br:27][CH2:28][C:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:8]([OH:9])[OH:16])=[O:30]

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 73297273HCID 73297273, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(50 g, 0.228 mol) of 2-aminophenyl boronic acid pinacol ester and (110 g, 0.798 mole) of potassium carbonate were charged into 10 L, 3 necks RBF connected with overhead stirrer, thermometer and additional funnel, 5 L of Chloroform, synthetic grade was loaded then stirred for 10±5 minutes at 25±5° C. after that (115 g, 50 mL, 0.57 mol) of Bromoacetyl bromide was added drop wise during 10±5 minutes while the mixture stirred. After end of loading, the mixture was stirred for 1-2 hrs at 25±5° C., the reaction completion was monitored by TLC (Ethyl acetate:n-hexane, 15:85 v/v). Afterward, 4-5 L of purified water was loaded then transferred to 10 L separatory funnel and steeled down for 10 minutes, chloroform layer (lower) was separated and dried over 50 g of sodium sulfate and filtered. The filtrate solution was concentrated under vacuum to dryness. The residue was recrystallized from diethyl ether to get pure 2-(bromoacetamido)phenylboronic acid intermediate, the product was characterized by 1H-NMR, 13C-NMR, mass and elemental analysis.

Aufarbeitung

  1. customRBF connected with overhead stirrer
  2. additionwas added drop wise during 10±5 minutes while the mixture
  3. stirringAfter end of loading, the mixture was stirred for 1-2 hrs at 25±5° C.
  4. customchloroform layer (lower) was separated
  5. dry with materialdried over 50 g of sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate solution was concentrated under vacuum to dryness
  8. customThe residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-bcbbc28f85c3442f9c5b2c2a25c38c4c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877980B2

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