Ethyl bromoacetate → HCID 71279395, compound

HRID 2171204Notes

Reaction equation

HRID 2171204 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:7]([OH:24])=[C:8]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[O:18][CH2:17]4)[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:31]([O:33][C:34](=[O:37])[CH2:35]Br)[CH3:32]>C(#N)C>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[O:18][CH2:17]4)[C:7]=2[O:24][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 67465720HCID 67465720, compound

Product 1

HCID 71279395HCID 71279395, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 5-(3-(cyclopropylmethoxy)-2-hydroxy-4-methoxyphenyl)isobenzofuran-1(3H)-one (250 mg, 0.766 mmol) in acetonitrile (20 mL) was added potassium carbonate (312 mg, 2.3 mmol) and ethylbromoacetate (256 mg, 1.533 mmol) and the reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT and filtered through celite. The filtrate was concentrated under reduced pressure to afford Ethyl 2-(2-(cyclopropylmethoxy)-3-methoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)acetate as a crude product which was used as such in further reaction (300 mg).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c253d63add64fc19d8f6941a9e72004
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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