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

HRID 1054673Notes

Reaction equation

HRID 1054673 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, 2 H), 7.25 (d, 2 H), 5.30-5.20 (m, 1 H), 420-4.00 (m, 2 H), 3.63 (s, 3 H), 2.70 (m, 1 H), 2.15 (m, 1 H).

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-cfcd092896be4bdd80e81666506f26f1
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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