Benzyl Bromide → 2-Amino-2'-benzyloxy-5-chlorobenzophenone

HRID 1419054Notes

Reaction equation

HRID 1419054 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5264882-Amino-5-chloro-2'-hydroxybenzophenone

Product 1

HCID 541754792-Amino-2'-benzyloxy-5-chlorobenzophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionThe mixture was subjected to extraction with 150 ml of water and 200 ml of ethyl acetate
  2. washthe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled off under reduced pressure
  5. customThe residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-2e09c85becd543e7b2b9d6a54a353619
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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