Water → [4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

HRID 549542Notes

Reaction equation

HRID 549542 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][Si](C(C)(C)C)(C)C)[CH:18]=[C:17]([Br:29])[CH:16]=2)=[CH:9][C:8]=1[CH3:30])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[Na+].[Na+].O>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([Br:29])[CH:16]=2)=[CH:9][C:8]=1[CH3:30])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 57791929HCID 57791929, compound

Product 1

HCID 57791915[4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

{4-[3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester 7 g, 13.3 mmol) was dissolved in THF under an atmosphere of nitrogen. Tetrabutylammonium fluoride 1 N in THF (15 mL) was added, and the reaction mixture was stirred at 60° C. for 2 h. Saturated sodium carbonate and water were added together with ethyl acetate, and the organic phase was separated. The organic phase was washed with water, dried, and evaporated to dryness. Yield: 3.2 g. HPLC-MS: m/z: 435.4 (M+Na); Rt: 2.22 min.

Workup

  1. customthe organic phase was separated
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e70a72f676134a4181cbb8c4e6637635
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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