Potassium Carbonate → Methyl 2-(4-bromo-3-methoxyphenoxy)propanoate

HRID 1773966Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH3:11][O:12][C:13](=[O:27])[CH:14](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][O:12][C:13](=[O:27])[CH:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][CH3:10])[CH:4]=1)[CH3:15]

Participants

Conditions

Temperature: 65 °C

Procedure

4-Bromo-3-methoxyphenol (209 mg, 1 mmol, 1 eq.) was dissolved in MeCN (4 mL). (±)-2-(Toluene-4-sulfonyloxy)-propionic acid methyl ester (258 mg, 1 mmol, 1 eq.) and K2CO3 (276 mg, 2 mmol, 2 eq.) were added and the mixture was stirred at 65° C. for 6 hours and further at r.t. for 4 days. The mixture was partitioned between water and Et2O. The layers were separated and the aq. phase was extracted with Et2O (2×). The comb. org. phases were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flashmaster (column: 25 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+20% AcOEt) to the title compound as a colorless oil.

Workup

customThe mixture was partitioned between water and Et2O
customThe layers were separated
extractionthe aq. phase was extracted with Et2O (2×)
dry with materialphases were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flashmaster (column: 25 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+20% AcOEt) to the title compound as a colorless oil

Sources & evidence

ORD record: ord-c3c60664ef0547a2863e6c97cf8b37a2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255090B2

Reaction notes

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