Dabco → HCID 86760543, compound

HRID 915552Notes

Reaction equation

HRID 915552 reaction equation
Br[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][P:5]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]([CH3:9])([CH3:8])[CH3:7].[CH2:18]1N2CCN(CC2)C1.[CH3:26][C:27]12[O:36][C:31]3([CH3:37])[O:32][CH:33]([CH2:35][C:29]([CH3:38])([O:30]3)[PH:28]1)[CH2:34]2>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:6]([P:5]([CH2:4][C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[P:28]1[C:29]2([CH3:35])[CH2:38][C:31]3([CH3:37])[O:32][C:33]([CH3:18])([CH2:34][C:27]1([CH3:26])[O:36]3)[O:30]2)[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 9237DabcoHCID 69501569[(2-Bromophenyl)methyl](di-tert-butyl)phosphaneHCID 69501576HCID 69501576, compound

Product 1

HCID 86760543HCID 86760543, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

2.5 g (7.9 mmol) of the thus obtained 2-bromobenzyl(di-tert-butyl)phosphine, 2.24 g DABCO (20 mmol), 1.94 g 1,3,5-trimethyl-4,6,9-trioxa-2-phosphatricyclo[3.3.1.1{3,7}]decane (9 mmol) and 0.23 g Pd(PPh3)4 (0.2 mmol) in 10 ml toluene were added into a 250 ml glass vessel under inert atmosphere, and the content of the vessel was heated to 140° C. under stirring for 12 hours. The mixture was than allowed to cool to 100° C., and was then filtered. The filtrate was cooled to room temperature, then 30 ml of methanol added were added and the mixture cooled for a period for 12 hours to −35+ C., 8-(2-{[di(tert-butyl)-phosphino]-methyl}phenyl)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.1{3,7}]decane was isolated as yellow crystals (2.2 g, 4.9 mmol, 62%), and could be characterized by showing two distinct resonance signals in 31P NMR at +38.08 and −38.96 ppm.

Workup

  1. temperatureto cool to 100° C.
  2. filtrationwas then filtered
  3. temperatureThe filtrate was cooled to room temperature
  4. addition30 ml of methanol added
  5. additionwere added
  6. temperaturethe mixture cooled for a period for 12 hours to −35+ C

Sources & evidence

ORD record
ord-cd425319fb9b4730abc1d744a80f1dd2
Source dataset
uspto-grants-2007_09
Patent number
US07265242B2

Reaction notes

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