Hydrochloric Acid → 2-Bromo-2',4'-difluoroacetophenone

HRID 1930035Notes

Reaction equation

HRID 1930035 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Br:9][CH2:10][C:11](Br)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:9][CH2:10][C:11]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[F:8])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97411,3-DifluorobenzeneHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27741852-Bromo-2',4'-difluoroacetophenoneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Difluorobenzene (100.0 g, 877 mmol) was added to a solution of bromoacetyl bromide (177.0 g, 870 mmol) and aluminum chloride (118.6 g, 890 mmol) in DCM (50 mL) at about 10-15° C. The reaction was then mixed at about 32° C. for about 2 h and then cooled and then added to 3N HCl (650 mL) at about 5-11° C. The solution was warmed to ambient temperature and the product was extracted with pentane (400 mL). The pentane was washed with pH 7 NaCl buffer, concentrated and filtered to afford the title compound (190.1 g, 91%). 1H NMR (DMSO-d6) δ 8.01 (m, 1 H), 7.46 (m, 1 H), 7.27 (m, 1 H), 4.82 (s, 2 H).

Workup

  1. additionThe reaction was then mixed at about 32° C. for about 2 h
  2. temperaturecooled
  3. extractionthe product was extracted with pentane (400 mL)
  4. washThe pentane was washed with pH 7 NaCl buffer
  5. concentrationconcentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-62138f9c97004a4eb784f3a25030af65
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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