Potassium Carbonate → 4-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-methoxy-benzoic acid ethyl ester

HRID 1255641Notes

Reaction equation

HRID 1255641 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]1[O:13][CH2:12][CH2:11][O:10]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[O:31][CH3:32])[CH3:21]>CS(C)=O.CCOC(C)=O>[CH2:20]([O:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH:9]3[O:10][CH2:11][CH2:12][O:13]3)[CH:4]=2)=[CH:26][C:25]=1[O:31][CH3:32])[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18920212HCID 18920212, compoundHCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenol

Product 1

HCID 579690074-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-methoxy-benzoic acid ethyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 2 (9.27 g, 37.83 mmol) in DMSO (50 mL) was added potassium carbonate (15.68 g, 113.48 mmol). The resulting mixture was stirred at rt for 30 min. followed by addition of compound 5 (8.99 g, 45.39 mmol). The resulting mixture was heated at 120° C., O/N. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to give crude product, which was purified by column chromatography (silica gel, 10% EtOAc in hexane) to afford the title compound 6 (5.6 g, 35%) as a pale yellow solid. 1H NMR 400 MHz (CDCl3) δ: 7.81 (d, J=9.0 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.35 (s, 1H), 6.97 (dd, J=8.6, 2.7 Hz, 1H), 6.60 (d, J=2.3 Hz, 1H), 6.49 (dd, J=8.6, 2.4 Hz, 1H), 6.01 (s, 1H), 4.39 (q, J=7.4 Hz, 2H), 4.20-4.01 (m, 4H), 3.81 (s, 3H), 1.40 (t, J=7.4 Hz, 3H); MS (ES) m/z: 423 (M+1)+, 425 (M+3)+.

Workup

  1. temperatureThe resulting mixture was heated at 120° C.
  2. washwashed with water (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude product, which
  6. customwas purified by column chromatography (silica gel, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-5d0536d5dca6451cbd5c87e70c9c9c1a
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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