Potassium Carbonate → HCID 67486710, compound

HRID 2371282Notes

Reaction equation

HRID 2371282 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]2[C:16](=[O:17])[O:15][C:14]([CH3:19])([CH3:18])[O:13][C:12]2=[O:20])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2([CH2:33][C:32]3[CH:35]=[CH:36][C:29]([Br:28])=[CH:30][CH:31]=3)[C:12](=[O:20])[O:13][C:14]([CH3:18])([CH3:19])[O:15][C:16]2=[O:17])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 67486385HCID 67486385, compound

Product 1

HCID 67486710HCID 67486710, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-benzoic acid methyl ester (3 g, 10.3 mmol) and K2CO3 (2.1 g, 15.4 mmol) in DMF (15 mL) was added 4-bromobenzyl bromide (3 g, 12.3 mmol). The solution was stirred at room temperature overnight. After partitioning between Et2O and water, the organic portion washed with brine, dried over Na2SO4 then concentrated to afford crude material which was crystallized from MeOH to afford 4-[5-(4-Bromobenzyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl]-benzoic acid methyl ester as a white solid (4.12 g, 87%). 1H NMR (500 MHz, DMSO-d6): δ 7.91 (d, J=8.5 Hz, 2H), 7.55 (d, J=8.5 Hz, 2H), 7.21 (d, J=8 Hz, 2H), 7.02 (d, J=8 Hz, 2H), 3.81 (s, 3H), 3.45 (s, 2H), 3.38 (s, 2H), 0.71 (s, 3H), 0.65 (s, 3H).

Workup

  1. customAfter partitioning between Et2O and water
  2. washthe organic portion washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated
  5. customto afford crude material which
  6. customwas crystallized from MeOH

Sources & evidence

ORD record
ord-712314fda20e4e8293650d5e9ef1e99b
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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