Benzyl Bromide → 2-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole

HRID 354725Notes

Reaction equation

HRID 354725 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCCCCC.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[Cl:1][C:2]1[S:3][C:4]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 14798Sodium HydroxideHCID 12953359(2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

Product 1

HCID 129533662-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazoleYield 81.2%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 4.34 g (0.02 mol) of the compound of Example 4, 14.1 g (0.0825 mol) of benzyl bromide, 0.1 g of Aliquat 336 (tradename of phase transfer catalyst available from the General Mills Co.) 25 ml of hexane, 15 ml of 50% sodium hydroxide, and 15 ml of water was held at reflux for 30 minutes. The hexane layer was separated, dried over MgSO4 and concentrated under reduced pressure. The residue (6.8 g) was Kugelrohr distilled at 2 mm (pot temperature 120°-130° C.) to give 5.0 g (81% yield) of 2-chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole nD25 1.5215.

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe hexane layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled at 2 mm (pot temperature 120°-130° C.)

Sources & evidence

ORD record
ord-348e8cff6958454aad5917a5310a6b32
Source dataset
uspto-grants-1983_03
Patent number
US04377054

Reaction notes

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