Bromine → HCID 70801735, compound

HRID 2038374Notes

Reaction equation

HRID 2038374 reaction equation
[Br:1]Br.C([O-])(=O)C.[K+].[C:8]([C:10]1[CH:11]=[C:12]([C:17]2[N:18]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:20][CH:21]=2)[CH:13]=[C:14]([F:16])[CH:15]=1)#[N:9].S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:21]1[S:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:18][C:17]=1[C:12]1[CH:13]=[C:14]([F:16])[CH:15]=[C:10]([C:8]#[N:9])[CH:11]=1

Participants

6

Reactant 4

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 517044Potassium Acetate2×HCID 70801511HCID 70801511, compound

Product 1

HCID 70801735HCID 70801735, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

At room temperature, 12.8 g (79.8 mmol) of bromine and 7.83 g (79.8 mmol) of potassium acetate are added to 2.21 g (7.98 mmol) of the compound from Example 24A in 75 ml of conc. acetic acid. The mixture is stirred at 100° C. for 12 h, whereby after 6 and 9 h the same amounts of bromine (in each case 12.8 g, 79.8 mmol) and potassium acetate (in each case 7.83 g, 79.8 mmol) are again added. A 1M aqueous sodium sulfite solution is subsequently added, and the reaction solution is extracted with dichloromethane. The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1). 2.31 g (78% of theory) of the title compound are obtained.

Workup

  1. extractionthe reaction solution is extracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-f76852003c524361aacc0fc57ee30967
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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