Water → (3-Bromophenyl)(4-methylphenyl)methanone

HRID 45480

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[Br:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[C:18](N(C)C)=[O:19].O>C1COCC1.CCCCC>[Br:14][C:15]1[CH:16]=[C:17]([C:18]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[O:19])[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: -80 °C

Procedure

To a solution of 38.5 g (0.225 mol) of 4-bromotoluene in 450 mL of THF, 300 mL (0.450 mol) of 1.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 hr at −80° C. This mixture was slowly warmed to room temperature and additionally stirred at this temperature for 30 min. To this mixture 52.0 g (0.23 mol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and then this mixture was stirred for 12 hr at room temperature. Later, 300 mL of water was added, organic solvent was evaporated using a rotary evaporator. The product was extracted with 2×200 mL of dichloromethane. The combined organic extracts were evaporated to dryness, and the residue was dried in vacuum. This procedure gave 51.3 g (83%) of 40 which was further used without additional purification.

Workup

temperatureThis mixture was slowly warmed to room temperature
stirringadditionally stirred at this temperature for 30 min
stirringthis mixture was stirred for 12 hr at room temperature
customorganic solvent was evaporated
customa rotary evaporator
extractionThe product was extracted with 2×200 mL of dichloromethane
customThe combined organic extracts were evaporated to dryness
customthe residue was dried in vacuum

Sources & evidence

ORD record: ord-559d82a387544e008795df8e74291c68
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541522B2

Linked notes

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