Potassium Carbonate → N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide

HRID 1927749

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1F)[CH:30]=[O:31]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:34]3[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][C:27]=3[Br:26])=[CH:12][CH:11]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

N-(4-chlorophenethyl)-4-hydroxybenzamide (1.5 g, 5.4 mmol) was diluted with DMSO (15 mL) followed by the addition of K2CO3 (0.89 g, 6.4 mmol) and 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol). The reaction was stirred at 85° C. overnight and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate and washed with twice with 10% sodium carbonate, water and brine, and then concentrated. The crude material was purified by silica gel chromatography eluting with hexanes:ethyl acetate (1:1) and then 100% ethyl acetate to yield N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide (1.6 g, 71% yield).

Workup

temperaturecooled to ambient temperature
washwashed with twice with 10% sodium carbonate, water and brine
concentrationconcentrated
customThe crude material was purified by silica gel chromatography
washeluting with hexanes:ethyl acetate (1:1)

Sources & evidence

ORD record: ord-1e7baa39cdbb4a42af63da61f22773e1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183289B2

Linked notes

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