Water → HCID 15578376, compound

HRID 544151Notes

Reaction equation

HRID 544151 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15](=[O:24])[CH:14]=2)=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15](=[O:24])[CH:14]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 12846663HCID 12846663, compound

Product 1

HCID 15578376HCID 15578376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (5.0 g) was added dropwise to a stirred solution of ethyl 6-(4-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate (5.48 g) in dichloromethane (40 ml) cooled to 0°-5° C. After 2 hours at below 5° C., water was cautiously added to the reaction mixture, with cooling, and the yellow solid which precipitated was filtered off. Recrystallisation from ethanol and then from ethyl acetate gave the title product as yellow crystals (mp 213°-215° C.).

Workup

  1. temperaturecooled to 0°-5° C
  2. temperaturewith cooling
  3. customthe yellow solid which precipitated
  4. filtrationwas filtered off
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-efc43760ce1a4cb4bf404ef4d2c48077
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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