Bromobenzene → 3-Bromo-1-(4-bromophenyl)propan-1-one

HRID 489219Notes

Reaction equation

HRID 489219 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>>[Br:12][CH2:13][CH2:14][C:15]([C:9]1[CH:10]=[CH:11][C:6]([Br:5])=[CH:7][CH:8]=1)=[O:16]

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 84944Propanoyl chloride, 3-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 123821193-Bromo-1-(4-bromophenyl)propan-1-oneYield 84.5%

Conditions

Temperature
50 °C

Procedure

AlCl3 (23.8 g, 178 mmol) was added by portions to bromobenzene (155 ml, 1.47 mol) at 0° C. 3-Bromopropionyl chloride (25 g, 146 mmol) was added dropwise to the red solution kept at 0° C. over 30 min. After 1 h at RT, the reaction mixture was heated to 50° C. for 1 h. After cooling, the mixture was poured over ice/water and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated to yield 3-bromo-1-(4-bromophenyl)propan-1-one (36 g) which was crystallized from petroleum ether (mp=66° C.). 1H NMR (CDCl3): 7.82 (2H, d, J=8.5 Hz), 7.62 (2H, d, J=8.5 Hz), 3.73 (2H, t, J=6.5 Hz), 3.55 (2H, t, J=6.5 Hz).

Workup

  1. waitAfter 1 h at RT
  2. temperatureAfter cooling
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-301e3bc9c0114939ad2d738ac3beaea7
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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