Benzyl Bromide → HCID 13558565, compound

HRID 652608Notes

Reaction equation

HRID 652608 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([Cl:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([Cl:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 108916751,4-dichloro-5-hydroxy-9,10-Anthracenedione

Product 1

HCID 13558565HCID 13558565, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mechanically stirred mixture of 177.2 g (0.605 mol) of 1,4-dichloro-5-hydroxy-9,10-anthracenedione (1, British Pat. No. 1,029,448), 83.5 g (0.605 mol) of powdered anhydrous potassium carbonate, 79 ml (0.675 mol) of benzyl bromide, and 1.7 l of dry acetone was heated at reflux for three days. The initial dark brown suspension changed to an olive green color signaling the end of the reaction. The mixture was filtered hot and the salts were washed with hot acetone. The cooled filtrate was concentrated to ~1/2 of its volume. The yellow precipitate was collected by filtration, washed with acetone and methanol, and dried at 200 mm/50° C./12 hr to leave 201.2 g (87%) of 2, mp 122°-126° C.

Workup

  1. temperatureat reflux for three days
  2. customthe end of the reaction
  3. filtrationThe mixture was filtered hot
  4. washthe salts were washed with hot acetone
  5. concentrationThe cooled filtrate was concentrated to ~1/2 of its volume
  6. filtrationThe yellow precipitate was collected by filtration
  7. washwashed with acetone and methanol
  8. customdried at 200 mm/50° C./12 hr

Sources & evidence

ORD record
ord-9628d64a65d4453cb77984bb810a20de
Source dataset
uspto-grants-1987_06
Patent number
US04672129

Reaction notes

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