HCID 14920724, compound → HCID 405000, compound

HRID 1824814Notes

Reaction equation

HRID 1824814 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=3)[S:8][C:4]=2[CH:3]=1>B(Br)(Br)Br.[Cl-].[Na+].O>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 14920724HCID 14920724, compound

Product 1

HCID 405000HCID 405000, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 25134Boron tribromideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-Bromo-2-(4-methoxy-phenyl)-benzothiazole (120 mg, 0.375 mmol) was suspended in boron tribromide (1M in methylene chloride, 7.0 mL) and stirred at room temp under nitrogen for 18.0 h. Reaction was poured into saturated brine and extracted with ethyl acetate. Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo. Residue was washed with hexane, and dried under vacuum yielding the title compound (115 mg, 100%) as a tan solid. Mass spec: MH+=306

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washEthyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine
  4. concentrationconcentrated in vacuo
  5. washResidue was washed with hexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1f7d31c612734bc4bc1ce74135241fc8
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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