Bromine → HCID 10566891, compound

HRID 877717Notes

Reaction equation

HRID 877717 reaction equation
[Br:1]Br.[C:3]([C:6]1([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:9][CH2:8][CH2:7]1)(=[O:5])[CH3:4]>C(O)C.CCCCCC>[CH2:13]([NH:12][C:10]([C:6]1([C:3](=[O:5])[CH2:4][Br:1])[CH2:9][CH2:8][CH2:7]1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 88924216HCID 88924216, compound

Product 1

HCID 10566891HCID 10566891, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

Bromine (0.593 mL, 11.51 mmol) was added dropwise to a 0° C. stirred solution of 1-acetyl-N-benzylcyclobutanecarboxamide (2.22 g, 9.60 mmol) in ethanol (35.5 mL). After 15 minutes, the ice bath was removed. The flask was sealed, and stirring was continued for 6.5 hrs. HPLC and LC/MS after 5 hrs indicated a complete or nearly complete reaction. The reaction was quenched by the addition of 25 mL of sat. aq NaHSO3 soluition. EtOAc was added (50 mL), the layers were separated, the aq layer was extracted with EtOAc (20 mL), the combined EtOAc layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give the crude product (2.80 g) as an oily yellow solid. The crude product was sonicated briefly in hexane. The ppt was collected by filtration, rinsed with hexane, and dried under vacuum to yield 2.33 g of the title compound as a pale yellow solid. LC/MS: m/e 312.08 (one of 2 Br-pattern peaks, M+H).

Workup

  1. customthe ice bath was removed
  2. customThe flask was sealed
  3. waitwas continued for 6.5 hrs
  4. waitHPLC and LC/MS after 5 hrs indicated
  5. customa complete or nearly complete reaction
  6. customThe reaction was quenched by the addition of 25 mL of sat. aq NaHSO3 soluition
  7. additionEtOAc was added (50 mL)
  8. customthe layers were separated
  9. extractionthe aq layer was extracted with EtOAc (20 mL)
  10. washthe combined EtOAc layers were washed with water, brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated under vacuum
  13. customto give the crude product (2.80 g) as an oily yellow solid
  14. filtrationThe ppt was collected by filtration
  15. washrinsed with hexane
  16. customdried under vacuum

Sources & evidence

ORD record
ord-ec3cb829f8e344e4a05ba4e7d0bd0f67
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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