Boron tribromide → 4-[5-(4-Hydroxyphenyl)thiazol-2-yl]benzoic acid

HRID 2270052Notes

Reaction equation

HRID 2270052 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:9][CH:8]=1>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:11][CH:12]=1.[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 18331084Methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate

Product 2

HCID 183310804-[5-(4-Hydroxyphenyl)thiazol-2-yl]benzoic acidYield 211.3%HCID 18331082Methyl 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of boron tribromide (1.0M in dichloromethane, 97.7 ml) was added dropwise methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate (3.18 g) in dichloromethane (50 ml) at −78° C. The reaction mixture was allowed to warm to room temperature, and stirred for 2 hours. The reaction mixture was poured into ice-water (1000 ml), and stirred for 30 minutes at room temperature. The precipitate was collected by filtration, washed with water, and dried overnight to give in the proportion of 37:63 mixture of methyl 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoate and 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoic acid (3.07 g), and those were used without purification in the next reaction.

Workup

  1. stirringstirred for 30 minutes at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight

Sources & evidence

ORD record
ord-8e353c564e2647b5802f8fa2ad8205c7
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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