Hydrochloric Acid → 1-Phenyl-3-(3,4-dihydroxy-5-trifluoromethylphenyl)prop-2-en-1-one

HRID 1195973Notes

Reaction equation

HRID 1195973 reaction equation
[C:1]1([C:7](=[O:23])[CH:8]=[CH:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([OH:20])=[C:12]([O:21]C)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.Cl>ClCCl>[C:1]1([C:7](=[O:23])[CH:8]=[CH:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([OH:20])=[C:12]([OH:21])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 540570871-Phenyl-3-(3-methoxy-4-hydroxy-5-trifluoromethylphenyl)prop-2-en-1-one

Product 1

HCID 540139591-Phenyl-3-(3,4-dihydroxy-5-trifluoromethylphenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 0.32 g of the above product obtained in Example 85 in 10 ml of dichloromethane 3 ml of 1 molar BBr3 --CH2Cl2 was added. The mixture was stirred for 20 min at room temperature, acidified with 10 ml 2 N hydrochloric acid and extracted with dichloromethane. The solvent was evaporated in reduced pressure and the residue crystallized from acetone-dichloromethane. Yield 0.07 g (23%), m.p. 196°-201° C.

Workup

  1. extractionextracted with dichloromethane
  2. customThe solvent was evaporated in reduced pressure
  3. customthe residue crystallized from acetone-dichloromethane

Sources & evidence

ORD record
ord-13ebe14ee2ce45408a7b1a5f7b25a7d2
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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