4-Chlorophenol → Phenol, 4-fluoro-, 1,1',1''-phosphite

HRID 1077566Notes

Reaction equation

HRID 1077566 reaction equation
[P:1]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[P:26]([O:43][C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)([O:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1.P(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.ClC1C=CC(O)=CC=1.P(Cl)(Cl)Cl.[P].FC1C=CC(O)=CC=1>C(N(CC)CC)C>[P:1]([O-:18])([O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1)[O:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1.[P:26]([O-:43])([O:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[O:35][C:36]1[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=1.[P:1]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([O:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[P:26]([O:43][C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)([O:35][C:36]1[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1

Participants

12

Reactant 7

HCID 46844-ChlorophenolHCID 97324-FluorophenolHCID 24387Phosphorus trichloride2×HCID 62550Diphenyl phosphiteHCID 620022Phenol, 4-fluoro-, 1,1',1''-phosphiteHCID 5462309PhosphorusHCID 5743262Phosphorous acid, tris(4-chlorophenyl) ester

Product 4

HCID 620022Phenol, 4-fluoro-, 1,1',1''-phosphiteHCID 5743262Phosphorous acid, tris(4-chlorophenyl) esterHCID 18515600Di(4-chlorophenyl) phosphiteHCID 19431395Di(4-fluorophenyl)phosphite

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Di(4-chlorophenyl) phosphite and di(4-fluorophenyl) phosphite were prepared from tris(4-chlorophenyl) phosphite and tris(4-fluorophenyl) phosphite, respectively using a previously described procedure (Walsh, E. N., Conversion of Tertiary Phosphites to Secondary Phosphonates. Diphenyl Phosphonate, J. Am. Chem. Soc. 1959, 81, 3023-6). Tris(4-chlorophenyl) phosphite was prepared from 4-chlorophenol and phosphorous trichloride with three equivalents of triethyl amine as a base using a modification of a previous procedure (McCombie, H., Saunders, B. C., Stacey, G. J., Esters Containing Phosphorus. Part I, J. Chem. Soc. 1945, 381). Similarly, tris(4-fluorophenyl) phosphite was prepared from 4-fluorophenol and phosphorous trichloride using one equivalent of triethyl amine as a base.

Sources & evidence

ORD record
ord-bbc132fab8804b82ad312ef9b2cedca0
Source dataset
uspto-grants-1996_08
Patent number
US05543396

Reaction notes

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