Bromine → HCID 71698261, compound

HRID 1752846Notes

Reaction equation

HRID 1752846 reaction equation
[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:5]1)=[N+:2]=[N-:3].C(O[Na])(C)=O.[Br:23]Br>C(O)(=O)C>[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:23])[CH:11]=2)[N:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 71698260HCID 71698260, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 71698261HCID 71698261, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of azide 12 (120 mg, 0.52 mmol) in acetic acid (2 ml) were successively added anhydrous AcONa (212 mg, 1.9 mmol) and Br2 (0.3 mL, 0.52 mmol). The mixture was stirred at 25° C. for 1 h and then quenched with water (30 mL). The resulting solution was extracted with CH2Cl2 (2×30 mL). The combined organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo. The residue was purified over column chromatography with petroleum ether/EtOAc (9:1 v/v) to give bromo azide 13 (153 mg) as thick liquid.

Workup

  1. customquenched with water (30 mL)
  2. extractionThe resulting solution was extracted with CH2Cl2 (2×30 mL)
  3. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified over column chromatography with petroleum ether/EtOAc (9:1 v/v)

Sources & evidence

ORD record
ord-3ef5edf3e58c49298203827f6fb5de73
Source dataset
uspto-grants-2015_10
Patent number
US09163038B2

Reaction notes

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