Ethyl bromoacetate → HCID 12898550, compound

HRID 1680250Notes

Reaction equation

HRID 1680250 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[OH:19].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:16][C:13]([F:14])([F:15])[C:8]([C:6]1[CH:5]=[C:4]([CH3:18])[C:3]([O:19][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:2]([CH3:1])[CH:7]=1)([OH:17])[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 706609HCID 706609, compound

Product 1

HCID 12898550HCID 12898550, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2,6-dimethyl-4-(hexafluoro-2-hydroxy-2-propyl)phenol [Farah, et al, J. Org. Chem., 30, 1003 (1965)], (10.0 g=35 mmol) in 100 ml acetonitrile add ethyl bromoacetate (6.9 g=42 mmol) and potassium carbonate (9.7 g=69 mmol). Stir 5 hours, filter and concentrate. Partition between ether and 1.0 N HCl. Dry and concentrate the ether extract. Recrystallize from ether-hexane to obtain, as white crystals, m.p. 99°-101° C., ethyl 2-[4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylphenoxy]acetate.

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. customPartition between ether and 1.0 N HCl
  4. customDry
  5. concentrationconcentrate the ether
  6. extractionextract
  7. customRecrystallize from ether-hexane

Sources & evidence

ORD record
ord-96274b977d754991bbd7e438bf638546
Source dataset
uspto-grants-1981_06
Patent number
US04272550

Reaction notes

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