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

HRID 1974723Notes

Reaction equation

HRID 1974723 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 2N 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-4b955bb7a37b442cb8902f551a83cb85
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

Loading…