Bromomethyl 2-methoxyphenyl ketone → HCID 59167790, compound

HRID 1616588Notes

Reaction equation

HRID 1616588 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[S:10])[NH2:9].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=O>C1COCC1>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:10][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[N:9]=1

Participants

4

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 23254886HCID 23254886, compound

Product 1

HCID 59167790HCID 59167790, compoundYield 142.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Add THF (125 mL, anhydrous) to a sealed vessel containing 5-thiocarbamoyl-pentanoic acid methyl ester (7.25 g, 41.4 mmol) and 2-bromo-2′-methoxyacetophenone (9.48 g, 41.4 mmol). Flush vessel with N2, seal, and heat at 80° C. overnight. Cool to room temperature, add EtOAc, wash with saturated aqueous NaHCO3 solution, brine, and backextract from each aqueous layer with EtOAc. Dry combined organic layers over MgSO4 and concentrate to get 18 grams of purple residue. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes to afford the title compound (9.7 g, 77%). TLC (30% EtOAc/hexanes) Rf=0.38. MS (IS) 306 (M+1)+.

Workup

  1. customFlush vessel with N2
  2. customseal
  3. temperatureCool to room temperature
  4. additionadd EtOAc
  5. washwash with saturated aqueous NaHCO3 solution, brine, and backextract from each aqueous layer with EtOAc
  6. customDry
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-c332ca81a1e34d91b68d9bc5be1ecc7a
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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