Triphenylphosphonium hydrobromide → {5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]benzyl}triphenylphosphonium bromide

HRID 1672633Notes

Reaction equation

HRID 1672633 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH2:8]O)[CH:7]=1.[BrH:20].[C:21]1([PH+:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[Br-:20].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH:7]=1)[CH2:8][P+:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 22178555Triphenylphosphonium hydrobromideHCID 57831395{5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanol

Product 1

HCID 86633687{5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]benzyl}triphenylphosphonium bromideYield 90.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5.95 g (22.86 mmol) of {5-fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanol from Example 31A in 130 ml of acetonitrile is mixed with 7.45 g (21.71 mmol) of triphenylphosphonium hydrobromide and heated to reflux for 3 hours. The reaction solution is then concentrated to dryness, and the resulting oil is taken up and triturated in diethyl ether. The product crystallizes as a white solid during this. After filtration, the solid is dried in a drying oven at 50° C. overnight. 11.5 g (77% yield) of crystalline product are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction solution is then concentrated to dryness
  4. customtriturated in diethyl ether
  5. customThe product crystallizes as a white solid during this
  6. filtrationAfter filtration
  7. customthe solid is dried in a drying oven at 50° C. overnight

Sources & evidence

ORD record
ord-60139f34638f4537ba945b8dc08de542
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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