Phenylboronic Acid → 4-bromo-1-(2,2-dimethylpropyl)-5-phenoxy-1H-benzotriazole

HRID 872295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872295
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 66827Phenylboronic AcidHCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

Produkt 1

HCID 679549744-bromo-1-(2,2-dimethylpropyl)-5-phenoxy-1H-benzotriazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6) (100 mg, 0.352 mmol, 1.0 equiv.), copper(II) acetate (63.9 mg, 0.352 mmol, 1.0 equiv.), phenylboronic acid (86 mg, 0.704 mmol, 2.0 equiv.) and freshly milled 4 Å molecular sieves were dried in vacuo and then suspended in anhydrous CH2Cl2 (3.5 mL) and TEA (245 μl, 1.760 mmol, 5.0 equiv.). The mixture was stirred ambient temperature for 18 hours, after which the mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified via reverse phase HPLC (water/acetonitrile gradient containing 0.1% TFA) to provide 422. 1H NMR (CDCl3) δ 7.42 (1H, d, J=8.87 Hz), 7.36-7.30 (2H, m), 7.21 (1H, d, J=8.87 Hz), 7.12-7.07 (1H, m), 6.95 (2H, dd, J=7.97, 1.44 Hz), 4.40 (2H, s), 1.06 (9H, s) ppm. LRMS m/z (M+H) 360.0 and 362.0 (intensity ratio ˜1:1) found, 360.1 and 362.1 required.

Aufarbeitung

  1. filtrationafter which the mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified via reverse phase HPLC (water/acetonitrile gradient containing 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-4b7d9bfc7c92402da28a606ccba46ff3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975286B2

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