Sodium Carbonate → HCID 87110705, compound

HRID 2175729Notes

Reaction equation

HRID 2175729 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([P:19](=[O:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl.CCCCCC>C(Cl)Cl>[Br:8][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:11]([O:10][CH3:9])=[CH:12][C:13]=1[P:19](=[O:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 21226440Methylenechloride HexaneHCID 86690453HCID 86690453, compound

Product 1

HCID 87110705HCID 87110705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

NBS (6.7 g, 37.6 mmol) was added to a solution of (3,5-dimethoxyphenyl)diphenylphosphine oxide (12.3 g, 36.4 mmol) in CH2Cl2 (140 ml) at 0° C. The resulting suspension was stirred at 0° C. for 1 h. Na2CO3 (saturated, 40 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 (40 ml×2). The combined organic layer washed with brine and dried over MgSO4. It was filtered and the solvent was removed to give the crude product as a pale yellow solid (14.3 g, 94% yield). It was sufficiently pure for the next step. The pure sample was obtained by crystallization from CH2Cl2/Hexane (1/15). 1H NMR (300 MHz, CD2Cl2) δ: 7.73-7.67 (m, 4H), 7.62-7.56 (m, 2H), 7.53-7.46 (m, 4H), 6.69 (d, J=3 Hz, 1H), 6.57 (dd, J1=3 Hz, J2=14.1 Hz, 1H), 3.89 (s, 3H), 3.68 (s, 3H). 31P NMR (121.5 MHz, CD2Cl2) δ: 30.72.

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 (40 ml×2)
  5. washThe combined organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationIt was filtered
  8. customthe solvent was removed
  9. customto give the crude product as a pale yellow solid (14.3 g, 94% yield)

Sources & evidence

ORD record
ord-02bba351da2a4e34a3e03a5c39572bfa
Source dataset
uspto-grants-2015_06
Patent number
US09062085B2

Reaction notes

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