Boron tribromide → Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 2261775Notes

Reaction equation

HRID 2261775 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 7540952Ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 135509402Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (550 mg, 2 mmol) in dichloromethane (20 mL) at −80° C. is added BBr3 (5 mL, 1M solution in dichloromethane). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by addition of methanol and is concentrated. The residue is partitioned between EtOAc and 1N HCl. The organic layer is concentrated and purified by chromatography (0 to 30% EtOAc in hexanes) to give the title compound as a tan solid, (500 mg, 95%). LC-MS: 264 (M+1); 1H NMR (DMSO-d6) δ 10.22 (s, 1H), 7.82 (d, 2H), 6.86 (d, 2H), 4.27 (q, 2H), 2.64 (s, 3H), 1.29 (t, 3H).

Workup

  1. customThe reaction is quenched by addition of methanol
  2. concentrationis concentrated
  3. customThe residue is partitioned between EtOAc and 1N HCl
  4. concentrationThe organic layer is concentrated
  5. custompurified by chromatography (0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e62668d4637543c8bbb114c24c31b675
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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