Potassium Carbonate → (3-Chlorophenyl)methyl 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoate

HRID 1879103Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([Cl:18])[CH:20]=2)=[CH:7][C:3]=1[C:4]([O:6][CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([Cl:18])[CH:20]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-chloro-5-hydroxybenzoic acid (500 mg, 2.9 mmol) in DMF (20 ml) were added potassium carbonate (1.0 g, 7.3 mmol, 2.5 eq) and 3-chlorobenzyl bromide (0.8 ml, 6.1 mmol, 2.1 eq). The mixture was heated at 60° C. for 2.5 hours. On cooling the mixture was diluted with ethyl acetate (300 ml) and washed with water (2×100 ml) then brine (70 ml). Organic layer dried and evaporated in vacuo. The residue was purified by column chromatography (Biotage SP4, 100 g silica column) eluting with 0-30% ethyl acetate in hexanes to afford the title compound as a clear oil (1.16 g). MS (ES+) m/z 421 [M+H]+ (C21H1535Cl3O3). 1H-NMR (400 MHz, d6-DMSO) δ 5.19 (2H, s), 5.35 (2H, s), 7.26 (1H, dd, J 8.8, J 3.2), 7.40-7.56 (10H, m).

Workup

temperatureOn cooling the mixture
washwashed with water (2×100 ml)
customOrganic layer dried
customevaporated in vacuo
customThe residue was purified by column chromatography (Biotage SP4, 100 g silica column)
washeluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-2435a08e855945d5953b37f78e4a93ea
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314147B2

Reaction notes

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