5-Bromo-2-hydroxybenzophenone → 4-Bromo-2-(hydroxy-phenyl-methyl)-phenol

HRID 25826

Reaktionsgleichung

Reaktionsgleichung von HRID 25826
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([CH:10]([OH:11])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

Komponenten

4

Edukt 2

HCID 2290095-Bromo-2-hydroxybenzophenoneHCID 4311764Sodium borohydride

Produkt 1

HCID 121347074-Bromo-2-(hydroxy-phenyl-methyl)-phenolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.02 g (27 mmol, 3.9 eqv) NaBH4 was added cautiously at rt to a solution of 1.92 g (6.9 mmol) (5-Bromo-2-hydroxy-phenyl)-phenyl-methanone (18) in 70 ml dry MeOH. After stirring this solution for 2 h at rt the solvent was evaporated and the residue was taken up in 70 ml water and 70 ml Et2O. The aq. layer was extracted with Et2O and the comb. org. fractions were washed twice with water, dried over Na2SO4 and evaporated. Column chromatography (Hexanes/EtOAc (1+1)) yielded 1.88 g (6.7 mmol, 98%) 19 as a white solid: Rf (Hexanes/EtOAc (1+1)) 0.57; mp 96-97° C.; 1H NMR (500 MHz, CDCl3) δ 2.76 (d, 1H, J=3.15 Hz), 5.98 (d, 1H, J=3.00 Hz), 6.79 (d, 1H, J=8.67 Hz), 6.98 (dd, 1H, J1=2.21 Hz, J2=0.47 Hz), 7.28 (dd, 1H, J1=8.67 Hz, J2=2.36 Hz), 7.33-7.41 (m, 5H), 7.92 (s, 1H); LRMS (EI) m/z 278 (5), 276 (4), 262 (56), 261 (100), 260 (46), 259 (95), 181 (21), 180 (12), 153 (12), 152 (33), 77 (16), 76 (16), 63 (10); HRMS (EI) Calcd. for C13H11BrO2: 277.994241. Found: 277.993366.

Aufarbeitung

  1. customwas evaporated
  2. extractionThe aq. layer was extracted with Et2O
  3. washfractions were washed twice with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9c6a7501b6c74a4abf47292e44773a61
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858600B2

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