Sodium Chloride → 5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

HRID 2046543Notes

Reaction equation

HRID 2046543 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Na+].[Cl-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:18])[CH2:15][CH2:16]Cl)=[C:10]([F:19])[CH:9]=1>>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[C:10]([F:19])[CH:9]=1)[C:14](=[O:18])[CH2:15][CH2:16]2

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 594738271-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanone

Product 1

HCID 594738055-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-oneYield 55.6%

Conditions

Temperature
180 °C

Procedure

To a mixture of AlCl3 (37.5 g, 282.48 mmol) and NaCl (11 g, 188.32 mmol) was added 1-(4-bromo-2-fluoro-phenyl)-3-chloro-propan-1-one (5 g, 18.83 mmol) at 130° C. The reaction temperature was slowly increased to 180° C. and kept for 1 hour. It was cooled, the mixture was poured into ice and extracted twice with ethyl acetate (2×100 ml). The combined ethyl acetate phases were dried over Na2SO4 and evaporated to get the crude product which was purified by column chromatography (silica gel, 5-10% ethyl acetate/hexane) to give 2.4 g (55%) of the title compound as brown solid. MS: 229.2 (MH+, 1Br).

Workup

  1. temperatureIt was cooled
  2. additionthe mixture was poured into ice
  3. extractionextracted twice with ethyl acetate (2×100 ml)
  4. dry with materialThe combined ethyl acetate phases were dried over Na2SO4
  5. customevaporated
  6. customto get the crude product which
  7. customwas purified by column chromatography (silica gel, 5-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8fb2f50ec9ad472dbd2052a68a42fd5a
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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