Boron tribromide → HCID 68226713, compound

HRID 1952546Notes

Reaction equation

HRID 1952546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)=[N:8][C:7]=1[CH3:23])=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[N:8][C:7]=1[CH3:23])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 682267072-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 68226713HCID 68226713, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled solution of 2-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.84 g, 2.5 mmol) in Methylene chloride (10 mL) at 0° C. was added 1M solution of boron tribromide in dichloromethane drop wise over a minute. The reaction was warmed gently to ambient temperature over 2 hrs. The resultant reaction is poured gently on ice water (25 mL) and extracted with Methylene chloride (3×75 mL). The organic layers are combined, washed with sodium bicarbonate (50 mL), brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated to give 2-[3-(3-Hydroxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.63 g, 78.3%) as a light pink oil. MS m/e 322.4 (M+H+).

Workup

  1. customThe resultant reaction
  2. additionis poured gently on ice water (25 mL)
  3. extractionextracted with Methylene chloride (3×75 mL)
  4. washwashed with sodium bicarbonate (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e14e12c8554a4f69ba0665bb24cf86c1
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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