Bromine → Methyl 3-bromo-2-oxocycloheptanecarboxylate

HRID 450831Notes

Reaction equation

HRID 450831 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:9]([O:11][CH3:12])=[O:10].[Br:13]Br>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:8]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([C:9]([O:11][CH3:12])=[O:10])[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 288225Methyl 2-oxocycloheptane-1-carboxylate

Product 1

HCID 11507060Methyl 3-bromo-2-oxocycloheptanecarboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-oxo-1-cycloheptanecarboxylate (50 g, 294 mmole) was dissolved in carbon tetrachloride (200 mL) and chilled to 0° C. Bromine (46.8 g, 294 mmole) was added via addition funnel over ˜30 minutes. The cooling bath was then removed and the reaction was allowed to warm to rt. The reaction was stirred under nitrogen at room temperature for 4 days. After 4 days the solution was poured into a separatory funnel containing water (1 L). The organic was washed with water and dried over sodium sulfate. Removal of the solvent in vacuo gave (72.4 g, 291 mmole, 99% crude yield). The material was carried on without further purification.

Workup

  1. customThe cooling bath was then removed
  2. temperatureto warm to rt
  3. additionAfter 4 days the solution was poured into a separatory funnel
  4. additioncontaining water (1 L)
  5. washThe organic was washed with water
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent in vacuo
  8. customgave (72.4 g, 291 mmole, 99% crude yield)
  9. customThe material was carried on without further purification

Sources & evidence

ORD record
ord-cd6222b68bb04ca0b318f7079f360580
Source dataset
uspto-grants-2013_07
Patent number
US08486990B2

Reaction notes

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