Phenethyl bromide → HCID 46214970, compound

HRID 237289Notes

Reaction equation

HRID 237289 reaction equation
C(OC([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.C(OC(N1CC(OC2C=C(Br)C=CC=2O)(C)C1)=O)(C)(C)C.BrCCC1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:14]([CH:19]=1)[O:13][C:10]1([CH3:12])[CH2:11][NH:8][CH2:9]1

Participants

7

Reactant 4

HCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 67346914HCID 67346914, compoundHCID 67347111HCID 67347111, compound

Product 1

HCID 46214970HCID 46214970, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Preparation of 3-(5-Bromo-2-phenethyloxy-phenoxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester. A mixture of 3-(5-bromo-2-hydroxy-phenoxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (30 mg. 0.08 mmol), (2-bromoethyl)benzene (29 μL, 0.21 mmol), KI (42 mg, 0.25 mmol) and Cs2CO3 (82 mg, 0.25 mmol) in 3 mL DMF was stirred at rt for 18 h. The reaction mixture was diluted with H2O and extracted with EtOAc (3×). The organic layers were dried and purified by RP HPLC (Agilent) to give the title compound as an oil (22 mg, 58%). MS (ESI): mass calcd. for C23H28BrNO4, 462.4; m/z found, 408.0 [M-56+H]+. 1H NMR (CDCl3): 7.38-7.18 (m, 5H), 7.07 (dd, J=8.6, 2.3 Hz, 1H), 6.76-6.74 (m, 2H), 4.24-4.08 (m, 4H), 3.84 (d, J=9.7 Hz, 2H), 3.11 (t, J=7.1 Hz, 2H), 1.58 (s, 3H), 1.45 (s, 9H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. customThe organic layers were dried
  3. custompurified by RP HPLC (Agilent)

Sources & evidence

ORD record
ord-ea14b5e99d324b50a0c6154ad2036608
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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