Reaction #1726721

Reaction equation

benzyl 2-benzyloxy-5-bromobenzoate

morpholine

(2-biphenyl)di-tert-butylphosphine

sodium tert-butoxide

→

tert-butyl 2-benzyloxy-5-(morpholin-4-yl)benzoate

benzyl 2-benzyloxy-5-(morpholin-4-yl)benzoate

Solvents

toluene

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with brine
2. 2
   Dryingdried over Na2SO4
3. 3
   OtherAfter removal of solvent by rotoevaporation
4. 4
   Otherthe crude product is chromatographed

Procedure

A solution of 500 mg (1.26 mmol) of benzyl 2-benzyloxy-5-bromobenzoate, 132 μL (132 mg, 1.5 mmol) of morpholine, 6 mg of palladium(II) acetate, 8.5 mg of (2-biphenyl)di-tert-butylphosphine, and 170 mg, 1.76 mmol) of sodium tert-butoxide in 3 mL of toluene is heated at 85° C. for 2 hrs. The reaction mixture is then diluted with ethyl acetate, washed with brine and dried over Na2SO4. After removal of solvent by rotoevaporation, the crude product is chromatographed to give 121 mg (0.30 mmol) of benzyl 2-benzyloxy-5-(morpholin-4-yl)benzoate and 72 mg (0.20 mmol) of tert-butyl 2-benzyloxy-5-(morpholin-4-yl)benzoate.

Source