Bromine → 2-Bromo-7-chloro-3,4-dihydronaphthalen-1(2H)-one

HRID 1287581Notes

Reaction equation

HRID 1287581 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13]Br>C(=S)=S>[Br:13][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]1=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 2566777-Chloro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 122065262-Bromo-7-chloro-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a solution of 7-chloro-1-tetralone, 204.3 g, (1.1 moles), in carbon disulfide (1.08 liters) there is dropwise, with stirring, 176 g (1.1 moles) of bromine in 540 ml carbon disulfide at 0°-5° C. After stirring for an additional 30 minutes, the solvent is removed, giving a dark brown syrup, weighing 315 g. The crude product is used as is in the following step.

Workup

  1. customat 0°-5° C
  2. stirringAfter stirring for an additional 30 minutes
  3. customthe solvent is removed
  4. customgiving a dark brown syrup

Sources & evidence

ORD record
ord-d1851919117d47388cc46d028467cc9e
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Reaction notes

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