Triphenylphosphonium hydrobromide → HCID 86634294, compound

HRID 1672670Notes

Reaction equation

HRID 1672670 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13]O.[BrH:21].[C:22]1([PH+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[Br-:21].[C:35]1([P+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=2[C:2]([F:20])([F:19])[F:1])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 22178555Triphenylphosphonium hydrobromideHCID 57864427HCID 57864427, compound

Product 1

HCID 86634294HCID 86634294, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4.913 g (17.41 mmol) of [2-(2-trifluoromethylbenzyloxy)phenyl]methanol from Example 80A in 70 ml of acetonitrile is mixed with 5.675 g (16.54 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. 9.621 g (88% 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-44a13a736647481db7d86e18c0561399
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…