Cesium carbonate → 1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester

HRID 1039110Notes

Reaction equation

HRID 1039110 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1)=[O:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 688451721-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3.26 g caesium carbonate and 1.01 g methyl 1-hydroxy-2-naphthoate in 10 ml abs. DMF was added 1.21 g 1-bromomethyl-4-trifluoromethyl-benzene and the mixture was reacted for 3 h at room temperature. The reaction was partitioned between water and ethyl acetate and the aqueous layer was extracted with ethyl acetate twice. The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The resulting residue was purified by chromatography (silica, heptane) to yield 1.62 g of 1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester.

Workup

  1. customthe mixture was reacted for 3 h at room temperature
  2. customThe reaction was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by chromatography (silica, heptane)

Sources & evidence

ORD record
ord-d8e640ee29b44a91b2b103197ead0018
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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