Boron tribromide → 3-Chloro-4-(1,3-thiazol-2-yloxy)phenol

HRID 404876Notes

Reaction equation

HRID 404876 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([O:14]C)[CH:11]=[CH:10][C:3]=1[O:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:3]=1[O:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 694346862-Chloro-4-methoxyphenoxy-1,3-thiazole

Product 1

HCID 691693943-Chloro-4-(1,3-thiazol-2-yloxy)phenolYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 9A (5.4 g, 0.022 mol) in dichloromethane at −78° C. was added a solution of BBr3 (0.066 mol) drop wise and the reaction mixture was stirred overnight while warming up to room temperature. The mixture was poured into ice and then stirred at room temperature for 24 hours. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under vacuum to give 3.5 g of product as an off-white solid (70% yield). 1H NMR (300 MHz, CDCl3) δ ppm 6.59 (dd, J=8.82, 2.94 Hz, 1H) 6.67 (d, J=2.57 Hz, 1H) 6.88 (d, J=3.68 Hz, 1H) 7.07 (d, J=8.82 Hz, 1H) 7.19 (d, J=3.68 Hz, 1H). MS (ESI) M/z 227.9 (M+H)+.

Workup

  1. additionThe mixture was poured into ice
  2. stirringstirred at room temperature for 24 hours
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5edc334af9cf42219776df681bd3a2e6
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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