Dimethylformamide → 3,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate

HRID 363091Notes

Reaction equation

HRID 363091 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([OH:17])=[C:12]([Cl:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][C:27]=1[O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C)C=O>O>[C:1]([O:9][C:10]1[CH:11]=[C:12]([Cl:18])[C:13]([O:17][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[C:27]([O:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:28]=2)=[C:14]([Cl:16])[CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 184293864-Benzoyloxy-2,6-dichlorophenol

Product 1

HCID 538852383,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoateYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 1.54 g of 3,5-dichloro-4-hydroxyphenyl benzoate, 0.83 g of potassium carbonate, 1.53 g of 4-fluoro-3-phenoxybenzyl bromide, and 10 ml of N,N-dimethylformamide, followed by stirring at room temperature for 5 hours. The reaction mixture was poured into water, and extracted twice with 50 m of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 2.32 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate (88% yield).

Workup

  1. extractionextracted twice with 50 m of diethyl ether
  2. washThe combined ether layer was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product

Sources & evidence

ORD record
ord-e9fb65c8b77949c79dedd97b2d5c88f9
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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