Salicyl Alcohol → HCID 57864427, compound

HRID 1672669Notes

Reaction equation

HRID 1672669 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:10][C:11]([F:20])([F:21])[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 5146Salicyl AlcoholHCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 57864427HCID 57864427, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.42 g (19.47 mmol) of 2-hydroxybenzyl alcohol in 100 ml of dry acetonitrile is mixed with 3.91 g (19.47 mmol) of 2-trifluoromethylbenzyl bromide and 2.96 g (21.42 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 5.08 g (87% yield) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-a9fa40a46dc044a9803a1de51d8dd7c7
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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