Bromine → HCID 11961662, compound

HRID 1354573Notes

Reaction equation

HRID 1354573 reaction equation
[C:1]([C:4]1([CH2:14][CH3:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[Br:16]Br>CO>[Br:16][CH2:2][C:1]([C:4]1([CH2:14][CH3:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[CH2:5]1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 21106104HCID 21106104, compound

Product 1

HCID 11961662HCID 11961662, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3.8 g of 2-acetyl-2-ethyl-5-fluoroindan and 35 ml of methanol were placed into a round-bottomed flask equipped with a thermometer, a mechanical stirrer and a dropping funnel. The reaction mixture was cooled in a cooling bath while stirring to a temperature between −5° C. and −8° C. and 0.7 ml of a Br2-solution in a small amount of methanol was added dropwise. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled to a temperature between −5° C. and −8° C. and an additional 0.175 ml of Br2-solution in a small amount of methanol was added dropwise. The cooling bath was removed and the reaction mixture was stirred at room temperature for an additional 1 to 2 hours. After chromatographic purification using methylene chloride as an eluent 2.51 g of 2-bromo-1-(2-ethyl-5-fluoro-indan-2-yl)-ethanone was obtained as a liquid (yield 69%).

Workup

  1. customequipped with a thermometer, a mechanical stirrer and a dropping funnel
  2. temperatureThe reaction mixture was cooled in a cooling bath
  3. additionwas added dropwise
  4. customThe cooling bath was removed
  5. temperatureThe reaction mixture was cooled to a temperature between −5° C. and −8° C.
  6. additionan additional 0.175 ml of Br2-solution in a small amount of methanol was added dropwise
  7. customThe cooling bath was removed
  8. stirringthe reaction mixture was stirred at room temperature for an additional 1 to 2 hours
  9. customAfter chromatographic purification

Sources & evidence

ORD record
ord-b4fe1a16d6144df79db15a84c3e90d01
Source dataset
uspto-grants-2007_05
Patent number
US07223871B2

Reaction notes

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