Triethylamine → HCID 59560629, compound

HRID 885685Notes

Reaction equation

HRID 885685 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([S:13][CH2:14][C:15](OCC)=[O:16])=[CH:6][C:5]=1[Br:20].COC(=O)C1C=C([N+]([O-])=O)C(F)=CC=1Br.CCN(CC)CC.C(OC(=O)CS)C>C(Cl)Cl.CCOC(C)=O>[Br:20][C:5]1[C:4]([C:3]([OH:2])=[O:21])=[CH:9][C:8]2[NH:10][C:15](=[O:16])[CH2:14][S:13][C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 43449031Benzoic acid, 2-bromo-4-fluoro-5-nitro-, methyl esterHCID 59560637HCID 59560637, compound

Product 1

HCID 59560629HCID 59560629, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-4-ethoxycarbonylmethylsulfanyl-5-nitro-benzoic acid methyl ester. To a 0° C. solution of 2-bromo-4-fluoro-5-nitro-benzoic acid methyl ester (4.8 g, 17.3 mmol) in CH2Cl2 (87 mL) was added Et3N, followed by mercapto-acetic acid ethyl ester, and the resulting mixture was stirred at RT for 4 h. The mixture was diluted with EtOAc (250 mL), washed with brine (50 mL), dried (MgSO4), and concentrated. The crude material was purified on SiO2 (0-35% EtOAc/hexanes) to provide 5 g (77%) of the title compound. 1H NMR (500 MHz, CDCl3): 8.75 (s, 1H), 7.79 (s, 1H), 4.24 (q, J=7.2, 2H), 3.96 (s, 3H), 3.78 (s, 2H), 1.30 (t, J=7.2, 3H).

Workup

  1. washwashed with brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude material was purified on SiO2 (0-35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dcc0d66a234b4e32929ca02a771be546
Source dataset
uspto-grants-2012_08
Patent number
US08242275B2

Reaction notes

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