Water → (4-Bromophenyl)(4-hydroxy-2-methylphenyl)methanone

HRID 229149Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:11]=2[CH3:18])=[O:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[CH3:18])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (4-bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone (27) (1.12 g, 3.67 mmoL) in benzene (25 mL) was added AlCl3 (1.98 g, 14.85 mmol). The mixture was heated at 90° C. for 3 h. Upon cooling, water (25 mL) was added, and the mixture was extracted with Et2O. The organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography on silica gel (EtOAc:hexanes) to yield 1.32 g (86%) of compound 28. 1H NMR (400 MHz, DMSO-d6): δ 2.26 (s, 3H), 6.63 (dd, J=2.4 Hz, 8.4 Hz, 1H), 6.72 (d, J=2.2 Hz, 1H), 7.18 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H), 10.10 (s, 1H).

Workup

temperatureUpon cooling
extractionthe mixture was extracted with Et2O
dry with materialThe organics were dried with MgSO4
concentrationconcentrated
customThe crude material was purified by chromatography on silica gel (EtOAc:hexanes)

Sources & evidence

ORD record: ord-30e9343238ae407c812c3c698ca94915
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560589B2

Reaction notes

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