Sodium Dithionite → HCID 10202877, compound

HRID 892291Notes

Reaction equation

HRID 892291 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 10276259HCID 10276259, compound

Product 1

HCID 10202877HCID 10202877, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-[3,5-dibromo-4-(3-nitrobenzyloxy)phenyl]propionic acid (0.66 g, 1.44 mmol) and Na2S2O4 (2.0 g, 11.5 mmol) in ethanol (50 mL, 90%) was stirred at 70° C. over night. The reaction mixture was concentrated and purified on column (silica gel, chloroform/methanol, 9:1), to give 0.18 g (29%) of 3-[3,5-dibromo-4-(3-amino-benzyloxy)phenyl]propionic acid. MS: m/z 429.1 (M+−1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on column (silica gel, chloroform/methanol, 9:1)

Sources & evidence

ORD record
ord-cc6e2dd96b56446da5812cbc4551d1eb
Source dataset
uspto-grants-2006_02
Patent number
US07005538B1

Reaction notes

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