Binap, (A+-)- → Diphenylphosphine

HRID 276166

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]([P:7]([C:14]2[C:23]([C:24]3[C:33]([P:34]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:32][CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.C1(C2C3C(=CC=CC=3)C=CC=2)C(O)=CC=C2C=1C=CC=C2>>[CH:38]1[CH:37]=[CH:36][C:35]([P:34]([C:33]2[C:24]([C:23]3[C:14]([P:7]([C:4]4[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:15][CH:16]=[C:17]4[C:22]=3[CH:21]=[CH:20][CH:19]=[CH:18]4)=[C:25]3[C:30]([CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:31][CH:32]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:40][CH:39]=1.[C:8]1([PH:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 634876Binap, (A+-)-

HCID 27552601-(1-Naphthyl)-2-naphthol

Product 2

HCID 70017Diphenylphosphine

HCID 634876Binap, (A+-)-

Procedure

U.S. Pat. No. 5,399,771 discloses a process for preparing BINAP starting from enantiomerically pure binaphthol which is firstly converted into the corresponding bis(trifluoromethanesulfonate). BINAP is subsequently obtained by nickel-catalysed coupling with diphenylphosphine. Disadvantages of this process are the high price and the difficulty of industrial handling of the sensitive and extremely aggressive trifluoromethanesulfonic anhydride in the preparation of binaphthol bis(trifluoromethanesulfonate). The use of other trifluoromethanesulfonic acid derivatives such as trifluoromethanesulfonyl fluoride or chloride is also difficult in process engineering terms due to the high volatility of the compounds (b.p.=−20° C. and 32° C., respectively).

Sources & evidence

ORD record: ord-bef01798f23d4267b8cf99b57a15f149
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353125B1

Linked notes

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