Boron tribromide dichloromethane → HCID 54439514, compound

HRID 1195954Notes

Reaction equation

HRID 1195954 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=[CH:15][C:16]([OH:18])=[O:17])[C:6]([Cl:11])=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.ClCCl>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=[CH:15][C:16]([OH:18])=[O:17])[C:6]([Cl:11])=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 540567045-(3,4-Dimethoxy-6-chlorophenyl)-2,4-pentadienoic acid

Product 1

HCID 54439514HCID 54439514, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution containing 0.54 g of the product obtained in Example 35 in 6 ml dichloromethane 6 ml of 1 molar boron tribromide-dichloromethane solution was added and stirred for 24 h at 20° C. The solvent was evaporated in vacuo and 2 N hydrochloric acid was added to the residue. The product was filtered and washed with water. Recrystallization from isopropanol-water yielded 0.22 g (46%) of the product desired, m.p. 203°-206° C.

Workup

  1. additionwas added
  2. customThe solvent was evaporated in vacuo and 2 N hydrochloric acid
  3. additionwas added to the residue
  4. filtrationThe product was filtered
  5. washwashed with water
  6. customRecrystallization from isopropanol-water

Sources & evidence

ORD record
ord-2ca25c8dc55b41849ee110dd5301cc9d
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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