Sodium Hydroxide → 1-[(2-Bromophenyl)sulfanyl]cyclohexanecarboxylic acid

HRID 1744083Notes

Reaction equation

HRID 1744083 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1([C:15]([O:17]C)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22235978Methyl 1-[(2-bromophenyl)sulfanyl]cyclohexanecarboxylate

Product 1

HCID 222359741-[(2-Bromophenyl)sulfanyl]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-[(2-bromophenyl)sulfanyl]cyclohexanecarboxylate (89 mg, in MeOH (3 mL) was added 1 M NaOH (1 mL). The mixture was stirred at room temperature for 2 days, then at 65° C. for 6 h. The mixture was then concentrated and the residue was partitioned between ethyl acetate and 1 M HCl. The organic phase was washed with brine, dried over MgSO4 and concentrated to give 1-[(2-bromophenyl)sulfanyl]cyclohexanecarboxylic acid.

Workup

  1. waitat 65° C. for 6 h
  2. concentrationThe mixture was then concentrated
  3. customthe residue was partitioned between ethyl acetate and 1 M HCl
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8eae0de17334900a2de9109a72d20fd
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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