Sodium Carbonate → 3-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic Acid Methyl Ester

HRID 1670074Notes

Reaction equation

HRID 1670074 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1.[C:27](=[O:30])([O-])[O-:28].[Na+].[Na+]>COCCOC.O.C1OC2C=CC(B(O)O)=CC=2O1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:5]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[C:8]([C:4]2[CH:9]=[CH:8][C:7]3[O:28][CH2:27][O:30][C:6]=3[CH:5]=2)[CH:9]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoate

Product 1

HCID 579059323-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic Acid Methyl EsterYield 198.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidSolvent

Procedure

3-Benzyloxy-5-trifluoromethanesulfonyloxy-benzoic acid methyl ester (15.4 g) was dissolved in 1,2-dimethoxyethane (250 mL), followed by addition of Pd(PPh3)4 (2.5 g), solution of sodium carbonate (12 g) in water (120 mL) and 3,4-methylenedioxyphenylboronic acid (8.4 g). The resulting reaction mixture was refluxed under the flow of nitrogen for 5 h. After cooling the organic layer was separated and washed with water and then dried over magnesium sulfate. The crude material was purified on a silica gel column using ethyl acetate and hexanes to yield 14.2 g (99% yield) of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed under the flow of nitrogen for 5 h
  3. temperatureAfter cooling the organic layer
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-71719f249d7b4f4da28739d19782df74
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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