Methyl 3-bromopropanoate → HCID 57475017, compound

HRID 1929410Notes

Reaction equation

HRID 1929410 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]>O1CCCC1>[CH3:26][O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:11][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 76934Methyl 3-bromopropanoateHCID 2724682Lithium diisopropylamideHCID 30174575-Bromo-2-methylbenzothiazole

Product 1

HCID 57475017HCID 57475017, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

5-Bromo-2-methylbenzothiazole (1000 mg) was dissolved in tetrahydrofuran (25 mL) and the mixture was cooled to −78° C. using an isopropanol/dry ice bath. Lithium diisopropylamide (1.5M in cyclohexane, 4.40 mL) was added, and the solution stirred for 30 minutes at −78° C. Methyl 3-bromopropionate (1.20 mL, 1836 mg) was added and the solution stirred at −78° C. for two hours. The reaction was quenched with 1M aqueous hydrochloric acid, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by flash column chromatography on silica gel using 10% ethyl acetate hexanes.

Workup

  1. stirringthe solution stirred at −78° C. for two hours
  2. customThe reaction was quenched with 1M aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography on silica gel using 10% ethyl acetate hexanes

Sources & evidence

ORD record
ord-9b5a6506cfcb4053b50d0fbd0a14f77c
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

Loading…