Bromine → HCID 13631740, compound

HRID 247740Notes

Reaction equation

HRID 247740 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[Br:13]Br>C(O)(=O)C.O>[Br:13][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:12]

Participants

5

Reactant 2

HCID 24408BromineHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 13631740HCID 13631740, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 4.3 g of 6-hydroxy-1-teralone in 0 ml of acetic acid and 6 ml of water with stirring under ice cooling is added dropwise a solution of 5.1 g of bromine in acetic acid for 8 minutes. After addition, the mixture is stirred unde ice cooling for 5 minutes and at room temperature for 30 minutes. To the reaction mixture is added 170 ml of ice-cold water. The insoluble substance is collected by filtration, dried and recrystallized from a mixture of hexane, ethyl acetate and ethanol to give 4.8 g of 5-bromo-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone, melting at 183°-186° C.

Workup

  1. additionAfter addition
  2. waitat room temperature for 30 minutes
  3. filtrationThe insoluble substance is collected by filtration
  4. customdried
  5. customrecrystallized from a mixture of hexane, ethyl acetate and ethanol

Sources & evidence

ORD record
ord-9c6919d4e38e4b2b992dcbe1f39c518a
Source dataset
uspto-grants-1987_11
Patent number
US04709095

Reaction notes

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