Binol → 13-Chloro-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene

HRID 259894

Reaction equation

HRID 259894 reaction equation
[P:1]([Cl:4])(Cl)Cl.[CH:5]1[CH:10]=[C:9]2[CH:11]=[CH:12][C:13]([OH:26])=[C:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][C:16]=3[OH:25])[C:8]2=[CH:7][CH:6]=1>>[P:1]1([Cl:4])[O:26][C:13]2[CH:12]=[CH:11][C:9]3[C:8]([C:14]=2[C:15]2[C:24]4[C:19]([CH:18]=[CH:17][C:16]=2[O:25]1)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:7][CH:6]=[CH:5][CH:10]=3

Participants

3

Reactant 2

HCID 11762BinolHCID 24387Phosphorus trichloride

Product 1

HCID 437207413-Chloro-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene

Procedure

The phosphinite-phosphites are synthesized as follows. Phosphorus trichloride is reacted with 1,1'-bi-2-naphthol to give the 1,1'-binaphthyl-2,2'-diyl phosphorochloridite. The chloridite is then reacted with either 1,1'-bi-2-naphthol or 2,2'-biphenol, followed by diphenylchlorophosphine. These reactions are all conducted stepwise in toluene with excess triethylamine present. The product is isolated by filtering off the triethylamine hydrochloride, then removing the solvent under reduced pressure.

Sources & evidence

ORD record
ord-45379f88daaf49e981146093f941ee62
Source dataset
uspto-grants-1996_06
Patent number
US05523453

Linked notes

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