Sodium Hydroxide → HCID 57444205, compound

HRID 1159349Notes

Reaction equation

HRID 1159349 reaction equation
[OH-].[Na+].[F:3][C:4]([F:18])([F:17])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]2[S:11]C(=O)[O:13][C:9]=2[CH:8]=1>C1COCC1>[F:18][C:4]([F:3])([F:17])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([SH:11])=[C:9]([OH:13])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57444206HCID 57444206, compound

Product 1

HCID 57444205HCID 57444205, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In some embodiments, the 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol can be generated by hydrolysis of 6-(2,2,2-trifluoroethoxy)benzo[d][1,3]oxathiol-2-one and used in the aforementioned step without isolation in a solid form. In one embodiment, the 6-(2,2,2-trifluoroethoxy)benzo[d][1,3]oxathiol-2-one can be hydrolyzed with aqueous sodium hydroxide to afford 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol. In an exemplary embodiment, the 6-(2,2,2-trifluoroethoxy)benzo[d][1,3]oxathiol-2-one dissolved in degassed THF can be hydrolyzed by addition of degassed aqueous sodium hydroxide; subsequently, the reaction can be quenched with acid and the resultant 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol can be obtained in organic solution. In some aspects, the 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol can be obtained in organic solution by partitioning the solvent mixture with degassed MTBE, extracting the remaining aqueous solution with degassed MTBE, and combining the organic layers containing 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol. The 5-(2,2,2-trifluoroethoxy)-2-mercaptophenol dissolved in the organic solution (THF/MTBE) can be used directly in the ring forming reaction without isolation.

Workup

  1. customsubsequently, the reaction
  2. customcan be quenched with acid

Sources & evidence

ORD record
ord-844e46cc31e9493cb0939057689c27bd
Source dataset
uspto-grants-2010_10
Patent number
US07812050B2

Reaction notes

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