Reaction #1895

Reaction equation

2-amino-5-chloro-2'-hydroxybenzophenone

potassium carbonate

benzyl bromide

→

2-amino-2'-benzyloxy-5-chlorobenzophenone

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   ExtractionThe mixture was subjected to extraction with 150 ml of water and 200 ml of ethyl acetate
2. 2
   Washthe ethyl acetate layer was washed with water
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled off under reduced pressure
5. 5
   OtherThe residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=10:1 to 5:1)

Procedure

In 30 ml of N,N-dimethylformamide was dissolved 5.0 g of 2-amino-5-chloro-2'-hydroxybenzophenone, as obtained in Example 123 (1), to which were added 4.2 g of potassium carbonate and 2.9 ml of benzyl bromide; the mixture was then stirred for 2 hours at room temperature. The mixture was subjected to extraction with 150 ml of water and 200 ml of ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=10:1 to 5:1) to yield 6.4 g of 2-amino-2'-benzyloxy-5-chlorobenzophenone as prism crystals, m.p. 110° to 111° C.

Source