Water → Benzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinate

HRID 1481785Notes

Reaction equation

HRID 1481785 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:41])C(=O)C1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([Br:41])[C:22]([OH:25])=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 71281752HCID 71281752, compound

Product 1

HCID 89421752Benzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzyl 2,4-bis(benzyloxy)-5-hydroxynicotinate (0.29 g, 0.66 mmol) and NBS (0.13 g, 0.72 mmol) in DMF (1.2 mL) was stirred at room temperature for 5 min then treated with water. The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-30% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinate (0.23 g, 68%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. custompurified by silica chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-21ba3dc850684b919a1ed23e40cc7feb
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…