Reaktion #54103

Reaktionsgleichung

SOCl2

5-Bromo-2-methoxy-benzoic acid

AlCl3

DMF

→

18

Ausbeute 181.2%

(5-bromo-2-hydroxy-phenyl)-phenyl-methanone

Ausbeute 181.2%

Lösungsmittel

CH2Cl2

toluene

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas evaporated
2. 2
   workup.DISSOLUTIONthe the crude acyl chloride was dissolved in 75 ml of dry benzene
3. 3
   workup.ADDITIONThis solution was then added cautiously
4. 4
   workup.ADDITIONAfter complete addition the resulting mixture
5. 5
   Temperaturwas refluxed for 5 h
6. 6
   Sonstigequenched
7. 7
   workup.ADDITIONby adding H2O and conc. hydrochloric acid
8. 8
   ExtraktionThe aq. layer was extracted with EtOAc
9. 9
   Trocknenfractions were dried over NaSO4
10. 10
    Sonstigeevaporated

Vorschrift

10.07 ml (138.8 mmol, 2.2 eqv) SOCl2 was added to a solution of 14.77 g (63.9 mmol) 5-Bromo-2-methoxy-benzoic acid (17) in 140 ml dry toluene, followed by 0.5 ml (6.5 mmol, 0.1 eqv) DMF. After stirring this solution for 1.5 h at 70° C. the solvent was evaporated and the the crude acyl chloride was dissolved in 75 ml of dry benzene. This solution was then added cautiously under stirring to a suspension of 10.30 g (77.3 mmol, 1.2 eqv) AlCl3 in 80 ml dry benzene at 10° C. After complete addition the resulting mixture was refluxed for 5 h and then quenched by adding H2O and conc. hydrochloric acid. The aq. layer was extracted with EtOAc and the comb. org. fractions were dried over NaSO4 and evaporated. Column chromatography (CH2Cl2) yielded 16.03 g (57.9 mmol, 90%) 18 as a yellow solid: Rf (CH2Cl2) 0.67; 1H NMR (500 MHz, CDCl3) δ 6.99 (d, 1H, J=8.99 Hz), 7.52-7.68 (m, 6H), 7.70 (d, 1H, J=2.36 Hz), 11.91 (s, 1H); LRMS (EI) m/z 278 (80), 277 (100), 276 (86), 275 (92), 201 (31), 200 (22), 199 (30), 198 (20), 105 (63), 77 (57), 63 (19); HRMS (EI) Calcd. for C13H9BrO2: 275.978591. Found: 275.977717.

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