HCID 86656159, compound → HCID 67258278, compound

HRID 1192466Notes

Reaction equation

HRID 1192466 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].[CH3:14][Mg]Br>O1CCCC1>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]([OH:13])[CH3:14]

Participants

4

Reactant 2

HCID 86656159HCID 86656159, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67258278HCID 67258278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-bromo-2-methyl-1,3-benzothiazole-5-carbaldehyde (1.70 g, 6.64 mmol) in tetrahydrofuran (30 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (9.48 mL) at 0° C. The reaction was stirred at room temperature for 30 minutes, quenched with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The crude residue was used directly in next step (1.81 g, 100%). LCMS calculated for C10H11BrNOS(M+H)+: m/z=272.0; found: 271.9.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a11475951e204ffaa09cf06a73101de2
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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