Boron tribromide → HCID 15578389, compound

HRID 544153Notes

Reaction equation

HRID 544153 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[O:4][C:3]=1[C:16]([O:18]CC)=[O:17].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[O:4][C:3]=1[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15578374HCID 15578374, compound

Product 1

HCID 15578389HCID 15578389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of ethyl 3-bromo-6-(2-chlorophenyl)-4-oxo-4H-pyran-2-carboxylate (2.3 g) and boron tribromide (2.5 ml) in dichloromethane (25 ml) was heated under reflux for 4 hours. A tan solid precipitated out. Water (25 ml) was added to the cooled mixture and the yellow solid was filtered off. Recrystallisation from glacial acetic acid yielded the title product as off-white needles (mp 205°-207° C. with decomposition).

Workup

  1. temperatureunder reflux for 4 hours
  2. customA tan solid precipitated out
  3. additionWater (25 ml) was added to the cooled mixture
  4. filtrationthe yellow solid was filtered off
  5. customRecrystallisation from glacial acetic acid

Sources & evidence

ORD record
ord-b8398551655d430e848f5270b35d6e14
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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