Water → 2-Bromo-1,3-benzothiazol-6-ol

HRID 563891Notes

Reaction equation

HRID 563891 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:5]=2[N:6]=1.B(Br)(Br)Br.O>ClCCl>[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

Product 1

HCID 451167822-Bromo-1,3-benzothiazol-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-bromo-6-methoxybenzothiazole (0.67 g) in dry dichloromethane (30 ml) at ambient temperature under an atmosphere of nitrogen was added dropwise a solution of boron tribromide in dichloromethane (5.5 ml, 1M). The mixture was stirred for 2 hours at ambient temperature, stored for 2 days then poured into water. The organic phase was separated, washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give 2-bromo-6-hydroxybenzothiazole as a pale pink solid, 0.60 g, m.p. 203-204° C.

Workup

  1. waitstored for 2 days
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-2a2ec4c282ac4da392f2ccb81d1b9f37
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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