Reacción #54116

Ecuación de reacción

4-bromo-anisaldehyde

1-Bromonaphthalene

n-Butyllithium

ether

→

(5-Bromo-2-methoxy-phenyl)-napthalen-1-yl-methanol

Rendimiento 88.2%

Disolventes

THF

—

hexanes

THF

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise via a dropping funnel
2. 2
   workup.WAITfor 2 h at −30° C.
3. 3
   Otrofinally 15 h
4. 4
   Otroat r.t
5. 5
   OtroAfter quenching
6. 6
   Otrothe reaction with 1 M aq. HCl-solution
7. 7
   Lavadophase was washed subsequently with water and brine before it
8. 8
   Secadowas dried over MgSO4
9. 9
   Otroevaporated

Procedimiento

To a solution of 1.70 ml (12.22 mmol) 1-Bromonaphthalene (61) in 40 ml dry THF 7.64 ml (12.22 mmol, 1.00 eq.) of a 1.6 M solution of n-Butyllithium in hexanes were added at −78° C. via syringe. After stirring this mixture for 1 h at −78° C. a solution of 2.63 g (12.23 mmol, 1.00 eq.) 4-bromo-anisaldehyde (60) in 30 ml dry THF was added dropwise via a dropping funnel. The resulting mixture was stirred for another 60 min at −78° C., then for 2 h at −30° C. and finally 15 h at r.t. After quenching the reaction with 1 M aq. HCl-solution and adding ether the org. phase was washed subsequently with water and brine before it was dried over MgSO4 and evaporated. Column chromatography (CH2Cl2) yielded 3.70 g (10.77 mmol, 88.15%) (5-Bromo-2-methoxy-phenyl)-napthalen-1-yl-methanol (62) as pale greenish foam. Rf (CH2Cl2)=0.37. 1H-NMR (500 MHz, CDCl3): δ=3.84 (s, 3H, OMe), 6.80 (d, J=8.51 Hz, 1H), 6.81 (s, 1H, HO—CH), 7.18 (d, 1H, J=2.68 Hz), 7.34 (dd, 1H, J1=8.82 Hz, J2=2.52 Hz), 7.42-7.48 (m, 3H), 7.55 (d, 1H, J=7.09 Hz), 7.79 (d, 1H, J=8.20 Hz), 7.83-7.87 (m, 1H), 7.96-8.00 (m, 1H). MS (EI): m/z=345 (14), 344 (76), 343 (17), 342 (77), 326 (14), 325 (12), 324 (14), 311 (10), 309 (10), 245 (25), 217 (12), 215 (88), 213 (84), 202 (19), 201 (12), 157 (18), 155 (37), 141 (21), 129 (66), 128 (100), 127 (42), 108 (12), 101 (24), 77 (14), 63 (11). HR-MS (EI): Calcd. for C18H15BrO2: 342.025541. Found: 342.025182.

Fuente