Cesium carbonate → 1227467-04-0

HRID 1850082Notes

Reaction equation

HRID 1850082 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12]S(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Br:23][C:24]1[CH:25]=[C:26](O)[CH:27]=[CH:28][CH:29]=1>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:23])[CH:29]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 673441901227467-04-0Yield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester (0.795 g, 3.16 mmol) and Cs2CO3 (1.13 g, 3.48 mmol) in DMF (30 mL) was added 3-bromophenol (0.547 g, 3.16 mmol). The reaction was heated to 80° C. for 18 h, then cooled to rt. Brine was added and the mixture extracted with Et2O (2×). The combined organics were washed with brine and dried. Silica gel chromatography (0-40% EtOAc in hexanes) gave 0.881 g (85%) of the title compound. MS (ESI): mass calcd. for C14H18BrNO3, 327.05; m/z found, 272.0 [M-56]+. 1H NMR (CDCl3): 7.17-7.11 (m, 2H), 6.90-6.88 (m, 1H), 6.70-6.66 (m, 1H), 4.89-4.82 (m, 1H), 4.30 (ddd, J=9.7, 6.4, 0.9 Hz, 2H), 3.99 (dd, J=10.3, 4.1 Hz, 2H), 1.45 (s, 9H).

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture extracted with Et2O (2×)
  3. washThe combined organics were washed with brine
  4. customdried

Sources & evidence

ORD record
ord-fc996ae025e545018f02b1a6bc70ad69
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

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