Sodium Carbonate → HCID 87111012, compound

HRID 2175731Notes

Reaction equation

HRID 2175731 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([P:19](=[O:36])([C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=2)[C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC.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:36])([C:28]1[CH:29]=[C:30]([CH3:35])[CH:31]=[C:32]([CH3:34])[CH:33]=1)[C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 21584099Diethylether hexaneHCID 86690454HCID 86690454, compound

Product 1

HCID 87111012HCID 87111012, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

NBS (13.5 g, 76 mmol) was added to a solution of (3,5-dimethoxyphenyl)bis(3,5-dimethylphenyl)phosphine oxide (30 g, 76 mmol) in CH2Cl2 (400 ml) at 0° C. The resulting suspension was stirred at 0° C. for 1 h. Na2CO3 (saturated, 300 ml) was added to quench the reactions. It was stirred at RT for 30 min and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (100 ml×2). The combined organic layer washed with water (150 ml×2), brine (200 ml×1) 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) which was sufficiently pure for the next step. The pure product (34.2 g, 93% yield) was obtained by crystallization from ether/Hexane (1/15). 1H NMR (300 MHz, CD2Cl2) δ: 7.32 (br, 2H), 7.28 (br, 2H), 7.21 (br, 2H), 6.67 (d, J=2.7 Hz, 1H), 6.52 (dd, J1=2.7 Hz, J2=14.1 Hz, 1H), 3.90 (s, 3H), 3.69 (s, 3H), 2.34 (s, 12H). 31P NMR (121.5 MHz, CD2Cl2) δ: 31.35.

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 (100 ml×2)
  5. washThe combined organic layer washed with water (150 ml×2), brine (200 ml×1)
  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) which

Sources & evidence

ORD record
ord-b7d6e8a820e342f69730aba430f5e3de
Source dataset
uspto-grants-2015_06
Patent number
US09062085B2

Reaction notes

Loading…