Diethyl Ether → [2-(TRIFLUOROMETHYL)PHENOXY]ACETIC ACID

HRID 491399Notes

Reaction equation

HRID 491399 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[OH-].[Na+].Br[CH2:15][C:16]([OH:18])=[O:17].C(OCC)C>CN(C=O)C.C(O)C.[Cl-].[Na+].O>[F:11][C:8]([F:9])([F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:15][C:16]([OH:18])=[O:17]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 679582-Trifluoromethylphenol

Product 1

HCID 16769485[2-(TRIFLUOROMETHYL)PHENOXY]ACETIC ACIDYield 57.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 2-hydroxybenzotrifluoride (3.00 g, TCI) in a mixture of DMF (16.5 ml) and ethanol (1.8 ml) was added with sodium hydroxide (1.5 g, WAKO) and bromoacetic acid (2.6 g, TCI), and the mixture was stirred at 85° C. for 24 hours. The reaction mixture was added with diethyl ether and saturated brine, and successively washed with 1 N aqueous hydrochloric acid and saturated aqueous sodium carbonate. The layer produced between the aqueous layer and oil layer was dried to obtain a crude product of the title compound (Compound No. CA54, 2.36 g).

Workup

  1. washsuccessively washed with 1 N aqueous hydrochloric acid and saturated aqueous sodium carbonate
  2. customThe layer produced between the aqueous layer and oil layer
  3. customwas dried

Sources & evidence

ORD record
ord-9811bd549e014f43be60e29d5a6c3a1a
Source dataset
uspto-grants-2009_05
Patent number
US07531533B2

Reaction notes

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