Sodium Carbonate → HCID 86690452, compound

HRID 2175727Notes

Reaction equation

HRID 2175727 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:12]1[C:11]([O:10][CH3:9])=[CH:16][C:15]([O:17][CH3:18])=[CH:14][C:13]=1[P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 86690451HCID 86690451, compound

Product 1

HCID 86690452HCID 86690452, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (NBS) (8.9 g, 50 mmol) was added to the solution of diethyl 3,5-dimethoxyphenylphosphonate (12.5 g, 45.6 mmol) in CH2Cl2 (150 ml) at 0° C. The resulting suspension was stirred at 0° C. for 6 h. Na2CO3 (saturated, 60 ml) was added to quench the reactions. It was stirred at RT for 30 min, the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (80 ml×1). The combined organic layer was washed with brine and dried over MgSO4. It was filtered and the solvent was removed to give the crude product as a pale yellow oil (14 g, 87% yield). It was sufficiently pure enough for the next step. The pure sample was obtained by chromatography. 1H NMR (300 MHz, CD2Cl2) δ: 7.16 (dd, J1=3.0 Hz, J2=15.3 Hz, 1H), 6.67 (d, J=3.0 Hz, 1H), 4.20-4.06 (m, 4H), 3.89 (s, 3H), 3.85 (s, 3H), 1.34 (t, J=7.2 Hz, 6H). 31P NMR (121.5 MHz, CD2Cl2) δ: 15.59. 13C NMR (75.5 MHz, CD2Cl2) δ: 159.77 (d, Jc-p=20.0 Hz), 157.66 (d, Jc-p=19.0 Hz), 131.49 (d, Jc-p=189.2 Hz), 112.04 (d, Jc-p=8.7 Hz), 105.52 (d, Jc-p=4.5 Hz), 103.51 (d, Jc-p=2.9 Hz), 62.73, 62.66, 56.78, 55.96, 16.34, 16.26.

Workup

  1. customto quench the reactions
  2. stirringIt was stirred at RT for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (80 ml×1)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationIt was filtered
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-54872caf7daa4873b9d60912c85f77c5
Source dataset
uspto-grants-2015_06
Patent number
US09062085B2

Reaction notes

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