Bromine → (5-Bromothiazol-2-yl)dicyclopropylmethanol

HRID 410532Notes

Reaction equation

HRID 410532 reaction equation
[Br:1]Br.[CH:3]1([C:6]([CH:13]2[CH2:15][CH2:14]2)([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[OH:7])[CH2:5][CH2:4]1.CC([O-])=O.[Na+]>C(O)(=O)C>[Br:1][C:10]1[S:9][C:8]([C:6]([CH:3]2[CH2:5][CH2:4]2)([CH:13]2[CH2:14][CH2:15]2)[OH:7])=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 49962381Dicyclopropyl(1,3-thiazol-2-yl)methanol

Product 1

HCID 67429273(5-Bromothiazol-2-yl)dicyclopropylmethanolYield 57.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.271 mL, 5.26 mmol) was added dropwise to a stirred mixture of the product of Step 1 (411 mg, 2.10 mmol) and NaOAc (863 mg, 10.5 mmol) in acetic acid (9.17 mL) and the mixture was stirred at room temperature for 4 h. The reaction was quenched with brine and the aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried (sodium sulfate), filtered, and concentrated. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give (5-bromo-1,3-thiazol-2-yl)(dicyclopropyl)methanol (329 mg, 1.20 mmol, 57% yield) as an off-white solid. MS APCI: [M-OH]+ m/z 255.9

Workup

  1. customThe reaction was quenched with brine
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5b572990bfcf4e0eb5238b64802f99b4
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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