Methylparaben → HCID 58825032, compound

HRID 270976Notes

Reaction equation

HRID 270976 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([C:19]([F:18])([F:28])[F:29])[CH:21]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzene

Product 1

HCID 58825032HCID 58825032, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.28 g (15 mmol) of 4-hydroxy-benzoic acid methyl ester in 30 mL of dimethylformamide (DMF) was added 5.38 g (16.5 mmol) of cesium carbonate (Cs2CO3), followed by 2.75 mL (18 mmol) of 3-(trifluoromethyl)-benzyl bromide, and the resulting heterogeneous mixture was stirred at rt overnight. The reaction mixture was filtered and concentrated, diluted with water and extracted with ethyl acetate, and the combined organic extracts were washed with water and brine, and concentrated to give 4.75 g of desired 4-(3-trifluoromethyl-benzyloxy)-benzoic acid methyl ester as indicated by 1H NMR and 19F-NMR (containing traces of residual 3-(trifluoromethyl)-benzyl bromide).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washthe combined organic extracts were washed with water and brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56adf647b52a4494bde16d7ca3acb40b
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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