Triphenylphosphine → 3-(4-Bromophenyl)-3-methyloxetane

HRID 1665780Notes

Reaction equation

HRID 1665780 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[CH2:11][O:12][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 124571492-(4-Bromophenyl)-2-methylpropane-1,3-diol

Product 1

HCID 592062203-(4-Bromophenyl)-3-methyloxetaneYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-Bromophenyl)-2-methylpropane-1,3-diol (100 mg, 0.41 mmol), triphenyl phosphine (210 mg, 0.82 mmol), and diisopropyl azodicarboxylate (160 μL, 0.82 mmol) were combined in toluene (2 mL) and irradiated in the microwave at 140° C. for 10 minutes. The mixture was directly purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to give 3-(4-bromophenyl)-3-methyloxetane (39 mg, 42%) 1H NMR (400 MHz, DMSO-d6) δ 7.38-7.34 (m, 2H), 7.26-7.22 (m, 2H), 4.82-4.80 (m, 2H), 4.55-4.54 (m, 2H), 1.62 (s, 3H).

Workup

  1. customirradiated in the microwave at 140° C. for 10 minutes
  2. customThe mixture was directly purified by silica gel chromatography
  3. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-39fa3d882f0c40b094cc490873293b07
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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