Phosphorus tribromide → 6-(Bromomethyl)benzo[d]thiazole

HRID 911325

Reaction equation

HRID 911325 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10]O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.P(Br)(Br)[Br:13]>C(OCC)C>[Br:13][CH2:10][C:7]1[CH:8]=[CH:9][C:4]2[N:3]=[CH:2][S:1][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178603856-(Hydroxymethyl)benzothiazole

Product 1

HCID 534069936-(Bromomethyl)benzo[d]thiazoleYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dissolve benzothiazol-6-yl-methanol (0.4 g, 2.55 mmol) in diethyl ether (10 mL) and add slowly a solution of phosphorus tribromide (0.7 g, 2.55 mmol) in diethyl ether (5 mL). Stir the reaction mixture for 2 h at ambient temperature, wash with brine, dry the organic phase over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the title compound as a white solid (0.5 g, 86%). MS (ES+) m/z: 229 (M+H)+.

Workup

  1. washwash with brine
  2. dry with materialdry the organic phase over anhydrous Na2SO4
  3. customevaporate the solvent
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

Sources & evidence

ORD record
ord-cc3fcbbff70244cc9db2baa5d51c899e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Linked notes

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