Dimethylformamide → HCID 67257558, compound

HRID 1039956Notes

Reaction equation

HRID 1039956 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)([C:12]1[S:16][CH:15]=NC=1)[CH3:11].C[N:28]([CH:30]=O)C>C(OCC)(=O)C>[Br:1][C:15]1[S:16][C:12]([C:10]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=2)([OH:9])[CH3:11])=[N:28][CH:30]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 67258522HCID 67258522, compound

Product 1

HCID 67257558HCID 67257558, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-bromosuccinimide (0.933 g, 5.24 mmol) was added to a solution of the product of Step 1 (1.15 g, 4.37 mmol) and DMF (8.73 ml). The resulting solution was stirred overnight at room temperature. The reaction was diluted with ethyl acetate and transferred to a separatory funnel. The organic layer was washed with aqueous saturated NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated. Flash chromatography (0-65% EtOAc/hexanes) afforded methyl 4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]benzoate (863 mg, 2.52 mmol, 57.7% yield) as a yellow solid. MS ESI: [M+H]+ m/z 343.9.

Workup

  1. customtransferred to a separatory funnel
  2. washThe organic layer was washed with aqueous saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-08d64c9fa0c34ea397bfe89e3bba12c7
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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