Triethylamine → 1-(4-Bromobenzoyl)azetidine

HRID 1643570Notes

Reaction equation

HRID 1643570 reaction equation
CCN(CC)CC.Cl.[NH:9]1[CH2:12][CH2:11][CH2:10]1.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[N:9]1([C:18]([C:17]2[CH:21]=[CH:22][C:14]([Br:13])=[CH:15][CH:16]=2)=[O:19])[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 12308726Azetidine hydrochloride

Product 1

HCID 595603461-(4-Bromobenzoyl)azetidineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Et3N (2.00 mL, 14.3 mmol) and azetidine hydrochloride (462 mg, 4.94 mmol) were added to a solution of 4-bromobenzoyl chloride (1.07 g, 4.88 mmol) in CH2Cl2 (20 mL). The mixture was stirred at room temperature for 2 hr, diluted with CH2Cl2 (100 mL), and washed with 1N aqueous HCl (100 mL), H2O (100 mL), and brine (100 mL). The organic layer was dried over MgSO4 and concentrated to give a colorless oil (1.10 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 7.53 (ddd, J=17.43, 6.57, 2.27 Hz, 4 H) 4.21-4.32 (m, 4 H) 2.32-2.40 (m, 2 H);); LCMS for C10H10BrNO m/z 241.00 (M+H)+.

Workup

  1. washwashed with 1N aqueous HCl (100 mL), H2O (100 mL), and brine (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eac3b48a06414921afe788a4d3f62206
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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