Bicarbonate Ion → 3-Bromo-5-chloropyridin-2-amine

HRID 335072Notes

Reaction equation

HRID 335072 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Br:9]Br.C(=O)(O)[O-].OS([O-])=O.[Na+]>C(Cl)(Cl)Cl>[Br:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 24408BromineHCID 661742-Amino-5-chloropyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 27639713-Bromo-5-chloropyridin-2-amineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 250 mL round-bottomed flask was charged with 5-chloropyridin-2-amine (80 g, 622.3 mmol) and CHCl3 (100 mL). Added bromine (31.98 mL, 622.3 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was poured into saturated bicarbonate and NaHSO3 and extracted with CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated to afford the title compound (113.8 g, 88.1% yield) as a tan solid. 1H NMR (d6-DMSO) δ 7.97 (d, 1H), 7.90 (d, 1H), 6.44 (bs, 2H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-014c893496e74cd29bc729cfbd079aa3
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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