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Sodium Hydroxide → Bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphine

HRID 1581624
Notes
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Reaction equation

HRID 1581624 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([P:17](=O)([C:25]2[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:28]([O:35][CH3:36])=[C:27]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:26]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Br:24])[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].Cl[SiH](Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:13]([C:9]1[CH:8]=[C:7]([P:17]([C:25]2[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:28]([O:35][CH3:36])=[C:27]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:26]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Br:24])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[O:11][CH3:12])([CH3:14])([CH3:15])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 12115809Bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphine oxide

Product 1

HCID 12115810Bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphineYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Procedure

Into a four-neck flask were weighed 28.81 g (44.9 mmol) of the bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphine oxide (6). The atmosphere of the reaction vessel which was fitted with a thermometer, a condenser tube, and a dropping funnel with a pressure-equalizing tube was completely replaced with nitrogen. Thereto were added 300 mL of toluene, 29.92 g (247.0 mmol) of N,N′-dimethylaniline, and 30.41 g (224.5 mmol) of trichlorosilane, followed by 15 hours of heating at reflux. After the completion of the reaction, the reaction mixture was poured into 180 mL of 25% sodium hydroxide aqueous solution at 0° C. to 10° C. After 30 minutes of stirring at room temperature, the layers were separated from each other. The water layer was extracted with toluene (100 mL). The combined organic layer was washed with 1N hydrochloric acid aqueous solution, water and brine and dried over anhydrous magnesium sulfate. Toluene was removed by evaporation and the residue was recrystallized from toluene-methanol to obtain the title compound (24.30 g, a white solid).

Workup

  1. customInto a four-neck flask were weighed
  2. customThe atmosphere of the reaction vessel which was fitted with a thermometer, a condenser tube, and a dropping funnel with a pressure-equalizing tube
  3. temperatureof heating
  4. temperatureat reflux
  5. customAfter the completion of the reaction
  6. customthe layers were separated from each other
  7. extractionThe water layer was extracted with toluene (100 mL)
  8. washThe combined organic layer was washed with 1N hydrochloric acid aqueous solution, water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customToluene was removed by evaporation
  11. customthe residue was recrystallized from toluene-methanol

Sources & evidence

ORD record
ord-20b25f5359be4f499023bd85b5100879
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06730629B2

Reaction notes

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