Water → HCID 10185719, compound

HRID 1069214Notes

Reaction equation

HRID 1069214 reaction equation
[Br:1]Br.[Br:3][C:4]1[C:13]2[S:14][C:15]([CH3:18])=[C:16]([CH3:17])[C:12]=2[C:11]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[CH:9]2.C([O-])(=O)C.[K+].O>C(O)(=O)C>[Br:1][C:23]1[CH:24]=[C:19]([C:11]2[C:12]3[C:16]([CH3:17])=[C:15]([CH3:18])[S:14][C:13]=3[C:4]([Br:3])=[C:5]3[C:10]=2[CH:9]=[CH:8][CH:7]=[CH:6]3)[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[C:22]=1[OH:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517044Potassium AcetateHCID 22665455HCID 22665455, compound

Product 1

HCID 10185719HCID 10185719, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.040 mL, 0.756 mmol) in acetic acid (0.5 mL) was added dropwise to a stirred suspension of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-nitro-phenol (0.20 g, 0.467 mmol), potassium acetate (0.228 g, 2.335 mmol) in acetic acid (4 mL). After 10 min, water was added and the reaction mixture was extracted with ether. Silica gel was added to the ether phase and the solvent was removed. The adsorbate was flashed (gradient: 95:5 to 85:15) to provide the title compound as a yellow solid (0.141 g, 60%): mp 129-130° C.: NMR (DMSO-d6); δ11.30 (s, 1H), 8.22 (d, J=8 Hz, 1H), 8.03 (s, 1H), 7.96 (s, 1H), 7.67 (quintuplet, J=4 Hz, 1H), 7.51 (d, J=4 Hz, 2H), 2.45 (s, 3H), 1.65 (s, 3H); MS (EI): 2 bromine isotope pattern 505 (40%), 507 (100%), 509 (50%); Anal. Calc. for C20H13Br2NO3S: C, 47.36; H, 2.58; N, 2.76. Found: C, 47.18; H, 2.55; N, 2.63.

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. additionSilica gel was added to the ether phase
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-070793f7672340e6a08f552e1e5f8e19
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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