N-bromobutanimide → (2-Bromo-5-((3-methyloxetan-3-yl)methoxy)-1,3-phenylene)dimethanol

HRID 237571Notes

Reaction equation

HRID 237571 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1([CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH2:24][OH:25])[CH:19]=[C:20]([CH2:22][OH:23])[CH:21]=2)[CH2:13][O:12][CH2:11]1>C(#N)C>[Br:8][C:19]1[C:20]([CH2:22][OH:23])=[CH:21][C:16]([O:15][CH2:14][C:10]2([CH3:9])[CH2:13][O:12][CH2:11]2)=[CH:17][C:18]=1[CH2:24][OH:25]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866972335-[(3-Methyl-3-oxetanyl)methoxy]-1,3-benzenedimethanol

Product 1

HCID 86697234(2-Bromo-5-((3-methyloxetan-3-yl)methoxy)-1,3-phenylene)dimethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NBS (212 mg) is added to ((5-((3-Methyloxetan-3-yl)methoxy)-1,3-phenylene)dimethanol (270 mg) in acetonitrile (5 mL) and the resulting mixture is stirred at room temperature for 3 h. The solvent is evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100) to give the title compound. LC (method 7): tR=0.76 min; Mass spectrum (ESI−): m/z=315 [M−H]−.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)

Sources & evidence

ORD record
ord-766626f468d04f1eaf036adc46f5ccc2
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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