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

HRID 83768Notes

Reaction equation

HRID 83768 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-4d4b9f2cc62f440d85250a33bb0ad9c3
Source dataset
uspto-grants-2014_09
Patent number
US08846753B2

Reaction notes

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