Hexane → HCID 86690457, compound

HRID 2175734Notes

Reaction equation

HRID 2175734 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([C:13]1[CH:14]=[C:15]([P:25](=[O:52])([C:36]2[CH:41]=[C:40]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:39]([O:46][CH3:47])=[C:38]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:37]=2)[C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=2)[CH:16]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]=1[O:19][CH3:20])([CH3:12])([CH3:11])[CH3:10].CCCCCC>C(Cl)Cl>[Br:8][C:27]1[C:28]([O:34][CH3:35])=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=1[P:25](=[O:52])([C:36]1[CH:37]=[C:38]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:39]([O:46][CH3:47])=[C:40]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:41]=1)[C:15]1[CH:16]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([O:19][CH3:20])=[C:13]([C:9]([CH3:10])([CH3:11])[CH3:12])[CH:14]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 86690456HCID 86690456, compound

Product 1

HCID 86690457HCID 86690457, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

NBS (206 g, 115.7 mmol) was added to a solution of bis(3,5-di-tert-butyl-4-methoxyphenyl)(3,5-dimethoxyphenyl)phosphine oxide (70 g, 112.4 mmol) in CH2Cl2 (350 mL) at 0° C. The resulting suspension was stirred at 0° C. for 1 h then was warmed to RT and stirred for 4 h. The reaction was monitored by TLC until no starting material remained. The solution was washed with conc. Na2CO3 (300 mL×2) at RT. The organic layer was separated and dried over MgSO4. It was filtered and the solvent was removed to give the crude product. Hexane (400 mL) was added and the solution concentrated to 300 mL. It became cloudy and a white solid precipitated. Another 100 mL of hexane was added. The suspension was stirred at RT for 2 h. It was filtered and the solid dried under vacuum to give the product as a colourless solid (64.4 g). A second crop (7.2 g) was obtained from the mother liquor. Overall yield=90.9%. 1H NMR (400 MHz, CDCl3) δ: 7.55 (d, J=13.2 Hz, 4H), 7.04 (dd, J1=13.2 Hz, J2=2.8 Hz, 1H), 6.65 (d, J=2.8 Hz, 1H), 3.88 (s, 3H), 3.77 (s, 3H), 3.68 (s, 6H), 1.36 (s, 36H). 31P NMR (162.0 MHz, CDCl3) δ: 32.4.

Workup

  1. temperaturethen was warmed to RT
  2. stirringstirred for 4 h
  3. washThe solution was washed with conc. Na2CO3 (300 mL×2) at RT
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationIt was filtered
  7. customthe solvent was removed
  8. customto give the crude product
  9. concentrationthe solution concentrated to 300 mL
  10. customa white solid precipitated
  11. additionAnother 100 mL of hexane was added
  12. stirringThe suspension was stirred at RT for 2 h
  13. filtrationIt was filtered
  14. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-8dcf921a21f94d959f299c4518b6ecc0
Source dataset
uspto-grants-2015_06
Patent number
US09062085B2

Reaction notes

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