1-Bromonaphthalene → HCID 22290126, compound

HRID 1270021Notes

Reaction equation

HRID 1270021 reaction equation
[Mg].Br[CH2:3][CH2:4]Br.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[P:26](Cl)(Cl)(Cl)=[O:27]>C1COCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([P:26](=[O:27])([C:4]2[CH:3]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 70011-BromonaphthaleneHCID 77304-BromoanisoleHCID 78391,2-DibromoethaneHCID 24813Phosphorus oxychlorideHCID 5462224Magnesium

Product 1

HCID 22290126HCID 22290126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of magnesium (125.2 g, 5.15 mol), 1,2-dibromoethane (0.1 g, 0.5 mmol) and dry THF (1 L) were stirred under a blanket of nitrogen at rt for 1 h. The mixture was brought to 65° C. and 1-bromonaphthalene (343.7 g, 1.66 mol) was added by drop. Once the reaction initiated, the heating was removed and the 1-bromonaphthalene addition was continued for 2 h at a rate to maintain 55° C. 4-Bromoanisole (623.5 g, 3.33 mol) was then added over 4 h. The temperature was adjusted to 65° C. and held for a further 3 h. Phosphorus oxychloride (255.5 g, 1.66 mol) was then added by drop to maintain a temperature of 50–60° C. over 6 hours. The temperature was then adjusted to 50° C. and held overnight. The reaction mixture worked up to afford bis(4-methoxy-phenyl)(1-naphthyl)phosphine oxide mixture as an amber solid (508 g, 79 yield %). 31P NMR (CDCl3): δ 37.49 (s, 3.0%), 35.32 (s, 2.4%), 33.64 (s, 31.1%), 30.37 (s, 50.8%), 19.59 (s, 12.7%).

Workup

  1. customwas brought to 65° C.
  2. customthe heating was removed
  3. additionthe 1-bromonaphthalene addition
  4. waitwas continued for 2 h at a rate
  5. temperatureto maintain 55° C
  6. customwas adjusted to 65° C.
  7. waitheld for a further 3 h
  8. temperatureto maintain a temperature of 50–60° C. over 6 hours
  9. customwas then adjusted to 50° C.
  10. waitheld overnight
  11. customto afford

Sources & evidence

ORD record
ord-a1909198ca33480e8d6992910d0292bb
Source dataset
uspto-grants-2007_04
Patent number
US07201957B2

Reaction notes

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