Hydrochloric Acid → 1-(4-Bromo-1-naphthalenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 1513385Notes

Reaction equation

HRID 1513385 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](=[O:32])[CH2:17][C:18]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)(O)[C:19]([F:22])([F:21])[F:20])=[CH:8][CH:7]=1.Cl>C1(C)C=CC=CC=1>[Br:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](=[O:32])[CH:17]=[C:18]([C:24]2[CH:25]=[C:26]([Cl:31])[CH:27]=[C:28]([Cl:30])[CH:29]=2)[C:19]([F:21])([F:22])[F:20])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 866732401-(4-Bromo-1-naphthalenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-1-butanone

Product 1

HCID 866461861-(4-Bromo-1-naphthalenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of thionyl chloride (0.5 g, 4.46 mmol) in toluene (2 mL) was added dropwise to the product of Step A (1.1 g, 2.23 mmol) in toluene (10 mL) at 65° C. The mixture was cooled to ambient temperature and then poured into 1N hydrochloric acid (50 mL). The resulting mixture was extracted with ethyl acetate (2×25 mL). The combined extracts were dried and evaporated to give the title product as an oil (1.0 g, 95% yield).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×25 mL)
  2. customThe combined extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-3514988e1fe2423c8aa69340baf6e4ac
Source dataset
uspto-grants-2012_07
Patent number
US08217180B2

Reaction notes

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