Acetic Acid → 3-Bromo-1-(2-chlorophenyl)propane-1,2-dione

HRID 216770Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[C:9](=[O:11])[CH3:10].C(O)(=O)C.[Br:17]Br>C(Cl)(Cl)Cl>[Br:17][CH2:10][C:9](=[O:11])[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(2-chlorophenyl)propane-1,2-dione (1.2592 g, 6.9 mmol), glacial acetic acid (0.20 mL, 3.4 mmol, 0.5 eq), and bromine (0.35 mL, 6.8 mmol, 1 eq) in CHCl3 (17 mL) was heated at 60° C. for 12 h. The mixture was concentrated under reduced pressure to provide 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. The yellow liquid was carried on crude without purification for the next step. 1H NMR (CDCl3) δ ppm 7.71 (1H, dd, J=7.8, 1.6 Hz), 7.53-7.59 (1H, m), 7.40-7.49 (2H, m), 4.52 (2H, s). Mass Spectrum (ESI) m/e=261.0 [M+1 (79Br)] and 262.9 [M+1 (81Br)].

Workup

concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-984d854282d940439c3cccc4949aa969
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193199B2

Reaction notes

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