2-Bromobenzenethiol → Methyl 1-[(2-bromophenyl)sulfanyl]cyclohexanecarboxylate

HRID 1744082Notes

Reaction equation

HRID 1744082 reaction equation
Br[C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[SH:28]>CO>[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 805982-BromobenzenethiolHCID 81531DiisopropylethylamineHCID 3518593Methyl 1-bromocyclohexanecarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 715 mg (3.2 mmol) of methyl 1-bromocyclohexane-1-carboxylate (J. Med. Chem. 1970, 13, 317) in MeOH (5 mL) was added diisopropylethylamine (0.9 mL, 5.2 mmol) and 2-bromobenzenethiol (0.55 mL, 4.7 mmol). The solution was heated to 65° C. under nitrogen for 2 h, then cooled and partitioned between ethyl acetate and 1 M HCl. The organic phase was washed twice with 1 M NaOH and brine, then dried over MgSO4 and concentrated. Purification by flash chromatography (10% EtOAc/hexanes) gave methyl 1-[(2-bromophenyl)sulfanyl]cyclohexanecarboxylate.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and 1 M HCl
  3. washThe organic phase was washed twice with 1 M NaOH and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-84ab38f8a04f4529a461ba679cfb7d3b
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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