Prop-2-en-1-yl 4-(bromomethyl)benzoate → HCID 19605229, compound

HRID 1603637Notes

Reaction equation

HRID 1603637 reaction equation
Br[CH2:2][C:3]1[CH:14]=[CH:13][C:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])=[CH:5][CH:4]=1.[C:15]([O-:18])(=[S:17])[CH3:16].[K+]>CN(C)C=O>[C:15]([S:17][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])=[CH:5][CH:4]=1)(=[O:18])[CH3:16]

Participants

4

Reactant 2

HCID 19605361Prop-2-en-1-yl 4-(bromomethyl)benzoateHCID 23670855Potassium ethanethioate

Product 1

HCID 19605229HCID 19605229, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Allyl 4-(bromomethyl)benzoate (98 g, 0.4 moles) in dry dimethylformamide (100 ml) was added dropwise to a cooled suspension of potassium thioacetate (46 g, 0.4 moles) in dry dimethylformamide (200 ml). The cooling bath was removed and the mixture was stirred overnight. The reaction was poured into water and extracted with ethyl acetate (×3). The combined extracts were washed with water and brine. The mixture was dried and evaporated to give allyl 4-(acetylthiomethyl)benzoate as an orange oil (100 g, 100% yield). 1H NMR δ (CDCl3) 2.36 (3H, s, COCH3), 4.13 (2H, s, CH2), 4.82 (2H, m, CH2O), 5.32 (2H, m, CH2CH--), 6.05 (1H, m, CHCH2), 7.35 (2H, d, Ph-H), 7.98 (2H, d, Ph-H).

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured into water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined extracts were washed with water and brine
  5. customThe mixture was dried
  6. customevaporated

Sources & evidence

ORD record
ord-d9efaf3a24e0465ebb83fb80bf7230b2
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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