1-Bromodecane → (4-Decyloxyphenyl)phenyliodonium tosylate

HRID 703193Notes

Reaction equation

HRID 703193 reaction equation
F[Sb-](F)(F)(F)(F)F.[CH2:8]([O:18][C:19]1[CH:24]=[CH:23][C:22]([I+:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].BrCCCCCCCCCC.C1(OCCCCCCCCCC)C=CC=CC=1.[S:60]([C:72]1[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=1)([O:63][IH](C1C=CC=CC=1)=O)(=[O:62])=[O:61]>ClCCl.C(O)(=O)C>[S:60]([C:72]1[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=1)([O-:63])(=[O:62])=[O:61].[CH2:8]([O:18][C:19]1[CH:24]=[CH:23][C:22]([I+:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 81731-BromodecaneHCID 520713Decyloxybenzene2×HCID 16687828(4-Decyloxyphenyl)phenyliodonium hexafluoroantimonateHCID 178427798HCID 178427798, compound

Product 1

HCID 86743519(4-Decyloxyphenyl)phenyliodonium tosylateYield 67.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 1 was repeated to prepare (4-decyloxyphenyl)phenyliodonium hexafluoroantimonate. 1-bromodecane was used and the yield of decyl phenyl ether was 98.9%. In accordance with Example 1, 196 grams (0.5 mol) of phenyliodoso tosylate, 117 grams (0.5 mol) of the decyl phenyl ether, 50 ml of acetic acid and 200 ml of dichloromethane were stirred at 40° C. for 2 hours. The reaction mixture was filtered and a solution triturated with ether. The crystallized product was isolated by suction filtration and washed with ether and then dried under vacuum. There was obtained, 205.3 grams (67.5% yield of (4-decyloxyphenyl)phenyliodonium tosylate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customa solution triturated with ether
  3. customThe crystallized product was isolated by suction filtration
  4. washwashed with ether
  5. customdried under vacuum
  6. customThere was obtained

Sources & evidence

ORD record
ord-b584eb2ed42c49fe8c52b4e5c3528138
Source dataset
uspto-grants-1991_01
Patent number
US04981881

Reaction notes

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