Bromine → HCID 86716488, compound

HRID 1747712Notes

Reaction equation

HRID 1747712 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][CH2:12][C:13]1[CH2:18][CH2:17][C:16](=[O:19])[NH:15][N:14]=1)=[O:10].BrBr>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16](=[O:19])[NH:15][N:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 86716487HCID 86716487, compound

Product 1

HCID 86716488HCID 86716488, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

458 g (1.740 mol) of the compound obtained in Example 1A were initially charged in acetic acid (2250 ml), and the mixture was warmed to 50° C. At this temperature, 98.16 ml (1.914 mol) of bromine were added dropwise with vigorous stirring, and stirring was then continued at 50° C. for 3 h. After cooling, the mixture was concentrated to dryness. The residue was stirred with saturated aqueous sodium bicarbonate solution (4800 ml). The mixture was then filtered and the precipitate was washed with a little water. The filtrate was extracted twice with ethyl acetate. The organic phases were combined, dried and concentrated. This gave 117 g of the target compound (25% of theory).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to dryness
  3. stirringThe residue was stirred with saturated aqueous sodium bicarbonate solution (4800 ml)
  4. filtrationThe mixture was then filtered
  5. washthe precipitate was washed with a little water
  6. extractionThe filtrate was extracted twice with ethyl acetate
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2e1160f26ae14a5da4402d3110e9d22f
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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