Methanol → 1-chloro-7-hydroxy-4-nitro-9H-xanthen-9-one

HRID 364178Notes

Reaction equation

HRID 364178 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:17]C)[CH:12]=3)[O:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:17])[CH:12]=3)[O:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 136890881-Chloro-7-methoxy-4-nitro-9H-xanthen-9-one

Product 1

HCID 136890891-chloro-7-hydroxy-4-nitro-9H-xanthen-9-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 10 g of 1-chloro-7-methoxy-4-nitro-9H-xanthen-9-one and 84 ml of a 1M solution of boron tribromide in dichloromethane in 280 ml of dichloromethane was stirred at room temperature under an argon atmosphere for 16 hours, and then it was treated with 100 ml of methanol, and stirred for three hours. The mixture was filtered to give a light green solid. Recrystallization from chloroformmethanol afforded the title compound, mp 290°-292° C.

Workup

  1. stirringstirred for three hours
  2. filtrationThe mixture was filtered
  3. customto give a light green solid
  4. customRecrystallization from chloroformmethanol

Sources & evidence

ORD record
ord-81c0d83bec0548e69712b630f7769f82
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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