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Water → 5-(Bromomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3h)-ol

HRID 1037092
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037092
[CH3:1][C:2]1([CH3:13])[O:6][B:5]([OH:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:3]1=2.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:39])C(=O)C1.O>C(Cl)(Cl)(Cl)Cl>[Br:39][CH2:12][C:10]1[CH:9]=[CH:8][C:4]2[B:5]([OH:7])[O:6][C:2]([CH3:13])([CH3:1])[C:3]=2[CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 768479533,3,5-Trimethylbenzo[c][1,2]oxaborol-1(3h)-ol

Produkt 1

HCID 768484375-(Bromomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3h)-olAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943
Carbon Tetrachloride
Lösungsmittel

Versuchsvorschrift

To a solution of 3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (5.0 g, 28.4 mmol) in CCl4 (50 mL) at rt was added benzoyl peroxide (0.7 g, 2.8 mmol) following by NBS (5.0 g, 28.4 mmol). The reaction mixture was refluxed overnight, cooled to rt and treated with water. The aqueous layer was extracted with EA (20 mL×3). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give the product (4.5 g, yield 62%) as yellow oil. MS: 255 & 257 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe aqueous layer was extracted with EA (20 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-912e419eba364566bf68def27f6694e5
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546357B2

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