Ethanol → HCID 10274026, compound

HRID 857155Notes

Reaction equation

HRID 857155 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([N+:20]([O-])=O)[CH:14]=2)=[C:7]([Br:23])[CH:6]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:33](O)C>CO.O>[Br:23][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:24])[CH:10]=[C:9]([Br:11])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]2[N:19]=[CH:33][NH:20][C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 21867239HCID 21867239, compound

Product 1

HCID 10274026HCID 10274026, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl[3,5-dibromo-4-(4-amino-3-nitrophenoxy)phenyl]acetate (1 g) was dissolved in methanol (10 mL) and hot solution of sodium dithionite (6.1 g) in water (30 mL) was added. The reaction mixture was refluxed for 26 hours, ethanol (255 mL) was added and the formed precipitate filtered off through a pad of celite. The filtrate was concentrated to a constant volyme of 20 mL to which formic acid (16 mL) was added. After reflux for 4 hours, the reaction mixture was cooled down to room temperature, the formed yellow precipitate filtered off and washed with methanol. Recrystallisation from ethanol gave 0.4 g (42%) of 3,5-dibromo-4-(5-benzimidazolyloxy)phenylacetic acid. 1H-NMR (300 MHz, DMSO-d6): δ 12.55 (br s, 1H), 9.47 (s, 1H), 8.27 (s, 1H), 7.88 (d, J=3.0 Hz, 1H), 7.70 (s, 2H), 6.97 (d, J=9 Hz, 1H), 6.34 (dd, J=8.9 Hz, J=3.1 Hz, 1H), 3.68 (s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 26 hours
  2. filtrationthe formed precipitate filtered off through a pad of celite
  3. concentrationThe filtrate was concentrated to a constant volyme of 20 mL to which formic acid (16 mL)
  4. additionwas added
  5. temperatureAfter reflux for 4 hours
  6. filtrationthe formed yellow precipitate filtered off
  7. washwashed with methanol
  8. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-dbb3494525844a4287d4eab397525c05
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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