Reaction #947711

Reaction equation

ethyl 6-bromo-2-naphthoate

DIBAL

→

6-bromo-2-naphthylmethyl alcohol

Yield 111.9%

Solvents

toluene

Conditions

Workup

1. 1
   OtherAfter 1 hour the reaction mixture was quenched with ethyl acetate
2. 2
   workup.ADDITIONThe mixture was diluted with ethyl acetate
3. 3
   Washwashed with 1.0 N HCl, water and brine
4. 4
   DryingThe organics were dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated

Procedure

To a solution of ethyl 6-bromo-2-naphthoate (7.90 g, 28.30 mmol) in 200 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (84.9 mL, 1.0 M in toluene, 84.91 mmol) via transfer needle over 20 minutes. After 1 hour the reaction mixture was quenched with ethyl acetate and the resulting mixture was allowed to warm to RT. The mixture was diluted with ethyl acetate and washed with 1.0 N HCl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated to give 7.51 g of 6-bromo-2-naphthylmethyl alcohol as a white solid and used without further purification in the oxidation (step c). 1H NMR (300 MHz; CDCl3): δ 4.86 (s, 2H); 7.50 (dd, J1=2.0 Hz, J2=8.0 Hz, 1H); 7.57 (d, J=2.0 Hz, 1H); 7.70 (d, J=9.0 Hz, 1H); 7.75 (d, J=8.0 Hz, 1H); 7.79 (s, 1H); 8.00 (d, J=2.0 Hz, 1H).

Source