Triphenylphosphonium hydrobromide → HCID 86634287, compound

HRID 1672626

Reaction equation

HRID 1672626 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23]O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BrH:27].[C:28]1([PH+:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[Br-:27].[C:41]1([P+:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:25])[F:26])=[CH:4][CH:5]=3)=[CH:10][CH:11]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 22178555Triphenylphosphonium hydrobromideHCID 57864370HCID 57864370, compound

Product 1

HCID 86634287HCID 86634287, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11.7 g (32.65 mmol) of [2-(4′-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]-methanol from Example 24A in 100 ml of acetonitrile is mixed with 10.64 g (31.02 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 oven at 50° C. overnight. 20.5 g (30 mmol, 92% 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 oven at 50° C. overnight

Sources & evidence

ORD record
ord-1688345c4c0943e1b1de7afc830d182a
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Linked notes

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