2-Chloroethyl formate → 3-[5-Bromo-2-(3-chloro-benzyloxy)-phenoxy]-3-methyl-azetidine

HRID 237285

Reaction equation

HRID 237285 reaction equation
C([N:14]1[CH2:17][C:16]([O:19][C:20]2[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)([CH3:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCOC=O>ClCCCl>[Br:26][C:24]1[CH:23]=[CH:22][C:21]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)=[C:20]([CH:25]=1)[O:19][C:16]1([CH3:18])[CH2:15][NH:14][CH2:17]1

Participants

4

Reactant 2

HCID 2467482-Chloroethyl formateHCID 673483531-Benzhydryl-3-[5-bromo-2-(3-chloro-benzyloxy)-phenoxy]-3-methyl-azetidine

Product 1

HCID 462149713-[5-Bromo-2-(3-chloro-benzyloxy)-phenoxy]-3-methyl-azetidineYield 71.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

The title compound from Step B (60 mg) was dissolved in DCE (10 mL) and chloroethylformate (0.2 mmol) was added. The mixture was heated at 80-100° C. for 1 h and concentrated. The residue was dissolved in MeOH (3 mL) and heated at 150° C. in a microwave reactor for another 1 h. The mixture was cooled to rt and purified via PTLC providing the title compound (30 mg). MS (ESI): mass calcd. for C17H17BrClNO2, 381.0; m/z found, 382.0 [M+H]+. 1H NMR (CDCl3): 7.43-7.23 (m, 4H), 7.12-7.06 (m, 1H), 6.86-6.78 (m, 2H), 5.12 (s, 2H), 4.24-4.16 (m, 2H), 3.78-3.67 (m, 2H), 1.67 (s, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (3 mL)
  3. temperatureheated at 150° C. in a microwave reactor for another 1 h
  4. temperatureThe mixture was cooled to rt
  5. custompurified via PTLC

Sources & evidence

ORD record
ord-dd072f025a254296a3caa4036aa28404
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Linked notes

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