N-bromobutanimide → 6-Bromo-7-hydroxychroman-2-one

HRID 1620023Notes

Reaction equation

HRID 1620023 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br:13][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[OH:1])[O:9][C:8](=[O:12])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2981307-Hydroxychromanone

Product 1

HCID 468354166-Bromo-7-hydroxychroman-2-oneYield 54.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Intermediate 1 (20 g) in acetonitrile (50 ml) was added with N-bromosuccinimide (20 g, WAKO) under ice cooling, and stirred for 10 minutes under ice cooling, and then stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then recrystallized from acetonitrile to obtain the title compound (15 g).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-dc0c4128f5c74da9b017499c0d4ff735
Source dataset
uspto-grants-2014_07
Patent number
US08772327B2

Reaction notes

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