Potassium Carbonate → HCID 21840916, compound

HRID 1739466Notes

Reaction equation

HRID 1739466 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1>CN(C=O)C>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[O:15][CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 21840965HCID 21840965, compound

Product 1

HCID 21840916HCID 21840916, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-benzyl-6-bromophenol (3.2 g, 12.2 mmol) in DMF (50 ml) was treated with K2CO3 (2.19 g, 15.9 mmol) and methyl 4-bromomethylbenzoate (3.21 g, 14.02 mmol). The reaction was stirred at ambient temperature overnight, filtered and partitioned between ethyl acetate and water. The organic phase was washed with water (4×), dried (MgSO4) and evaporated to give methyl 4-(2-benzyl-6-bromophenoxymethyl)benzoate (5.96 g), which was used without further purification. MS(CI+):411(M+H)+

Workup

  1. filtrationfiltered
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with water (4×)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f3ec8aad000940ddbbc2fcb781b7b1d2
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

Loading…