Dinitrofluorobenzene → Ethyl [(2,4-dinitrophenyl)thio]acetate

HRID 2255181Notes

Reaction equation

HRID 2255181 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Na].C(N(CC)CC)C.[SH:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C1COCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[S:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6264DinitrofluorobenzeneHCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 66591377Sodium benzophenone

Product 1

HCID 3422675Ethyl [(2,4-dinitrophenyl)thio]acetateYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 100 ml round-bottomed flask were placed 14.8 g (10 ml, 79.6 mmol) 2,4-dinitrofluorobenzene, THF (20 ml, freshly distilled from sodium benzophenone) and triethylamine (11.1 ml, 79.6 mmol). The reaction was cooled in an ice bath while 9.55 g (8.73 ml, 79.6 mmol) ethyl 2-mercaptoacetate dissolved in THF (10 ml) was added dropwise. The resulting nearly black solution was allowed to warm slowly to room temperature and stirred 18 hours. The reaction mixture was poured onto 150 ml ice and the resulting layers were separated. The aqueous phase was extracted with EtOAc (2×125 ml). The organic layers were combined and washed with water (100 ml), dried over MgSO4 and concentrated to dryness in vacuo to yield 16.9 g of red-brown solid (74.1% yield).

Workup

  1. customInto a 100 ml round-bottomed flask were placed
  2. additionwas added dropwise
  3. customthe resulting layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc (2×125 ml)
  5. washwashed with water (100 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-c12804a209614067b4e81ed44913e7e8
Source dataset
uspto-grants-1993_08
Patent number
US05238908

Reaction notes

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