تفاعل #54116

معادلة التفاعل

4-bromo-anisaldehyde

1-Bromonaphthalene

n-Butyllithium

ether

→

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

المردود 88.2%

المذيبات

THF

—

hexanes

THF

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise via a dropping funnel
2. 2
   workup.WAITfor 2 h at −30° C.
3. 3
   أخرىfinally 15 h
4. 4
   أخرىat r.t
5. 5
   أخرىAfter quenching
6. 6
   أخرىthe reaction with 1 M aq. HCl-solution
7. 7
   غسيلphase was washed subsequently with water and brine before it
8. 8
   تجفيفwas dried over MgSO4
9. 9
   أخرىevaporated

الإجراء التجريبي

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.

المصدر