4-{[3-(trifluoromethyl)benzyl]oxy}benzoyl chloride synthesis

4synthesis methods

Product Name:4-{[3-(trifluoromethyl)benzyl]oxy}benzoyl chloride
CAS Number:632366-17-7
Molecular formula:C15H10ClF3O2
Molecular Weight:314.69

632366-16-6 Synthesis

4-{[3-(trifluoromethyl)benzyl]oxy}benzoic acid

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4-{[3-(trifluoromethyl)benzyl]oxy}benzoyl chloride

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Yield:-

Reaction Conditions:

with oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane;

Steps:

38 Example 38: Synthesis [OF 6-CYCLOHEXYL-7-OXO-5- [4- (3-TRIFLUOROMETHYL-BENZYLOXY)-PHENYL]-] 4, [7-DIHYDRO-PYRAZOLO] [1, 5-a] pyrimidine-2-carboxylic acid

To a solution of 2.28 g (15 mmol) [OF 4-LAYDROXY-BENZOIC ACID NAETHYL 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)-BE71ZOIC ACID METHYL ESTER] as indicated [BY H] NMR [AND 19F-NMR] (containing traces of residual 3- (trifluoromethyl)-benzyl bromide). This product was used without any further purification in the synthesis of 6-cyclohexyl- 7-oxo-5-[4-(3-trifluoromethyl-benzyloxy)-phenyl]-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2- carboxylic acid (545), which was accomplished as depicted in the above scheme, via standard transformations that were previously described for the synthesis of 5- (4-Benzyloxy-phenyl)-6- cyclohexyl-7-oxo-4,7-dihydro-pyrazolo [[1,] 5-a] pyrimidine-2-carboxylic acid.

References:

WO2003/101993,2003,A1 Location in patent:Page 73-74

99-76-3 Synthesis

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References

402-23-3 Synthesis

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References

Benzoic acid, 4-[[3-(trifluoromethyl)phenyl]methoxy]-, methyl ester

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References