Pyridine → Isopropyl 5-(2-bromoethyl)thiophene-2-carboxylate

HRID 1528013Notes

Reaction equation

HRID 1528013 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:23][CH2:24][C:25]1[S:29][C:28]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:26]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:23][CH2:24][C:25]1[S:29][C:28]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 24408BromineHCID 57487060Isopropyl 5-(2-hydroxyethyl)thiophene-2-carboxylate

Product 1

HCID 57487061Isopropyl 5-(2-bromoethyl)thiophene-2-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromine (1.74 mL, 33.9 mmol) was added slowly to a solution of triphenylphosphine (8.9 g, 33.9 mmol) in CH2Cl2 (65 mL) at −40° C. After 1 h at −40° C., a solution of the alcohol from step 1 (6.6 g, 30.8 mmol) and pyridine (2.5 mL, 30.9 mmol) in CH2Cl2 (65 mL) was added via cannula. The mixture was allowed to warm to room temperature and was stirred overnight. The reaction was concentrated in vacuo to a brown slurry. The mixture was triturated with hexanes (150 mL) and stirred vigorously. The solids were removed by filtration and the filtrate was concentrated in vacuo to afford 6.2 g (73%) of isopropyl 5-(2-bromoethyl)thiophene-2-carboxylate.

Workup

  1. concentrationThe reaction was concentrated in vacuo to a brown slurry
  2. customThe mixture was triturated with hexanes (150 mL)
  3. stirringstirred vigorously
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-de89cbe687de44b08f3719e45270e3e2
Source dataset
uspto-grants-2015_07
Patent number
US09090584B2

Reaction notes

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