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

HRID 640657Notes

Reaction equation

HRID 640657 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-e6e47d854c3242e792753956df916eb1
Source dataset
uspto-grants-2010_04
Patent number
US07691902B2

Reaction notes

Loading…