Sodium Hydroxide → 7-Bromothieno[3,2-b]pyridine

HRID 1639662Notes

Reaction equation

HRID 1639662 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2O)[CH:3]=[CH:2]1.P(Br)(Br)([Br:13])=O.[OH-].[Na+]>>[Br:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[CH:2][S:1][C:9]=12

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 667211077-Bromothieno[3,2-b]pyridineYield 59.3%

Procedure

Heat thieno[3,2-b]pyridin-7-ol (5.00 g, 33 mmol) and phosphorus oxybromide (50 g, 174 mmol) together at 110° C. for 3 h. Pour the hot reaction mixture into a mixture of ice and 5 N NaOH and extract with CH2Cl2. Dry the organic portion over Na2SO4 and evaporate. Purify the resulting crude material using a silica gel chromatography column (hexane:EtOAC=3:1) to give the title compound (4.19 g, 59%). ES/MS m/z (81Br) 215 (M+).

Workup

  1. additionPour the hot reaction mixture
  2. extractionextract with CH2Cl2
  3. dry with materialDry the organic portion over Na2SO4
  4. customevaporate
  5. customPurify the resulting crude material

Sources & evidence

ORD record
ord-fc237494f64f4aea9ee3ba9a67666790
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

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