Potassium Carbonate → HCID 67486710, compound

HRID 1755177Notes

Reaction equation

HRID 1755177 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-2e739ff3e9ac46e29c3b35c0b24eeaad
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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