Hydrogen Bromide → HCID 12902573, compound

HRID 648123Notes

Reaction equation

HRID 648123 reaction equation
Br.C[O:3][C:4]1[C:5]2[CH:18]=[C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:15][C:6]=2[CH2:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1>O>[O:3]=[C:4]1[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[CH2:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:5]1=2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12740032HCID 12740032, compound

Product 1

HCID 12902573HCID 12902573, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Six milliliters of 47% hydrobromic acid was added to 0.51 g of methyl 11-methoxy-5H-dibenzo[a,d]cycloheptene-2-acetate obtained in Example 12, and the mixture was stirred at room temperature for 2 hours. After the reaction, water was added to the reaction mixture, and the mixture was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride, and the ether was distilled off. Recrystallization of the residue from n-hexane afforded 0.43 g of methyl 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-2-acetate as colorless needle-like crystals having a melting point of 111° to 112° C.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ether
  3. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  4. distillationthe ether was distilled off
  5. customRecrystallization of the residue from n-hexane

Sources & evidence

ORD record
ord-c4229d71f6404ac6af567a274cc11b32
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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