Bromine → HCID 58536745, compound

HRID 912619Notes

Reaction equation

HRID 912619 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:17]Br>CC(O)=O>[Br:17][C:8]1([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[C:9]1=[O:12]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 67127354HCID 67127354, compound

Product 1

HCID 58536745HCID 58536745, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

step b—To a solution of 109 (3 g, 10.7 mmol) and HOAc (40 mL) stirred at RT under N2 was added dropwise via cannula a solution of bromine (1.88 g, 605 μL, 11.7 mmol) in HOAc (20.0 mL) over 20 min. The solution was stirred for 1 h at RT then warmed reaction to 50° C. and stirred 1 h. An aliquot of neat bromine (100 μL) was added and heating continued. The total heating time was 2.5 h. The reaction mixture was poured over ice, partitioned between EtOAc and H2O and aqueous phase was neutralized with satd. aq. NaHCO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The product was purified by SiO2 chromatography eluting with hexanes to afford 3.8 g (quantitative) of 110.

Workup

  1. temperaturethen warmed
  2. customreaction to 50° C.
  3. stirringstirred 1 h
  4. temperatureheating
  5. waitThe total heating time was 2.5 h
  6. additionThe reaction mixture was poured over ice
  7. custompartitioned between EtOAc and H2O and aqueous phase
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe product was purified by SiO2 chromatography
  14. washeluting with hexanes

Sources & evidence

ORD record
ord-4a62213e4f384c1d907767c0f21472e8
Source dataset
uspto-grants-2011_09
Patent number
US08026253B2

Reaction notes

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