Bromine → 2-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

HRID 241451Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Add p-trifluoromethylpropiophenone (75 g, 360 mmol, 1.0 equiv) to acetic acid (375 mL). Add bromine (18.1 mL, 352 mmol, 0.98 equiv) in acetic acid (375 mL) in a drop-wise fashion over 45 minutes. After completion of the addition, warm the mixture to an internal temperature of 40° C., and stir for 90 minutes. Remove the volatile components under reduced pressure, and dissolve the residue in Et2O (300 mL). Treat with a saturated sodium bicarbonate aqueous solution (4×200 mL) being cautious of vigorous gas evolution. Separate the organic phase, and dry over MgSO4. Remove the solids by filtration; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound as a colorless oil which solidifies on standing (93 g, 92.0% yield). 1H NMR (400 MHz, d6-DMSO) δ 8.13 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 2H), 5.27 (q, J=6.5 Hz, 1H), 1.93 (d, J=6.5 Hz, 3H).

Workup

additionAfter completion of the addition
customRemove the volatile components under reduced pressure
dissolutiondissolve the residue in Et2O (300 mL)
additionTreat with a saturated sodium bicarbonate aqueous solution (4×200 mL)
customSeparate the organic phase
dry with materialdry over MgSO4
customRemove the solids
filtrationby filtration
customcollect the filtrate
concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record: ord-2c2f098707624a6c82c1bfd76b139940
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648200B2

Reaction notes

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