Chlorodiphenylphosphine → 2,2'-Bis((diphenylphosphaneyl)methyl)-1,1'-binaphthalene

HRID 260582Notes

Reaction equation

HRID 260582 reaction equation
[Br-].[Br-].C[N+]([CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][N+](C)(C)C)(C)C.Cl[P:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O>[C:35]1([P:34]([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=2[CH2:28][P:34]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 66180ChlorodiphenylphosphineHCID 152406912,2'-Bis[(trimethylammonio)methyl]-1,1'-binaphthyl dibromide

Product 1

HCID 109524072,2'-Bis((diphenylphosphaneyl)methyl)-1,1'-binaphthaleneYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 7 is repeated, but using an electrolyte comprising 5.58 g (0.010 mol) of 2,2'-bis[(trimethylammonio)methyl]-1,1'-binaphthyl dibromide, 6.62 g (0.030 mol) of chlorodiphenylphosphine and 50 ml of dimethyl formamide (max. 0.1% of water) in the electrolysis. The amount of charge is 0.96 Ah. Workup gives 5.1 g of 2,2'-bis[(diphenylphosphino)methyl]-1,1'-binaphthyl ("naphos"). This corresponds to a yield of 78% based on 2,2'-bis[(trimethylammonio)methyl]-1,1'-binaphthyl dibromide used.

Workup

  1. additionThe amount of charge

Sources & evidence

ORD record
ord-dd9484e3951b4fe3aed5a2c96b9edc99
Source dataset
uspto-grants-1996_06
Patent number
US05527967

Reaction notes

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