Triethylamine → 2-(4-Bromophenyl)-1-(methylsulfonyl)azetidine

HRID 338330Notes

Reaction equation

HRID 338330 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:11][CH2:10][N:9]2[S:20]([CH3:19])(=[O:22])=[O:21])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 655792352-(4-Bromophenyl)azetidine

Product 1

HCID 866986772-(4-Bromophenyl)-1-(methylsulfonyl)azetidineYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-bromophenyl)azetidine (200 mg, 0.808 mmol) and triethylamine (98 mg, 0.97 mmol) in anhydrous dichloromethane (6 mL) was added methanesulfonyl chloride (111 mg, 0.97 mmol). The mixture was stirred at rt for 5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, concentrated in vacuo to give the title compound (200 mg, 85% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ7.50 (d, 2H), 7.25 (d, 2H), 5.30-5.20 (m, 1H), 420-4.00 (m, 2H), 3.63 (s, 3H), 2.70 (m, 1H), 2.15 (m, 1H).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad05d5f6d98f43be98f662d62ac8d9c0
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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