Dihydrocoumarin → 6-Bromochroman-2-one

HRID 256410

Reaction equation

HRID 256410 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[Br:12]Br>C(=S)=S>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[O:1][C:2](=[O:11])[CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 660DihydrocoumarinHCID 24408Bromine

Product 1

HCID 2667376-Bromochroman-2-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 74.08 g (0.50 mole) 2-chromanone in 150 ml carbon disulfide at 0° C. was added dropwise over 15 minutes, 79.91 g (0.50 mole) bromine. Stirring was continued at 0° C. for ten minutes and at room temperature for 2 days. The resulting mixture was filtered, the crystals air dried to afford 96.8 g (85%) of colorless material, m.p. 103°-105° C. (2 crops).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe crystals air dried

Sources & evidence

ORD record
ord-025aa8f96f58419ba8e011645c002d95
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Linked notes

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