HCID 21996962, compound → HCID 70149291, compound

HRID 1976326Notes

Reaction equation

HRID 1976326 reaction equation
BrC1C=[CH:6][C:5]([O:8]C(C)C)=[C:4](C(C2C=CC(C)=CC=2)=C)C=1.BrC1C=CC(CC(=O)C)=C(C(C2C=CC(C)=CC=2)=C)C=1.[Br:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[C:44]([C:49]([C:51]2[CH:52]=[C:53]([CH3:57])[CH:54]=[CH:55][CH:56]=2)=[CH2:50])[CH:43]=1>>[Br:41][C:42]1[CH:47]=[CH:46][C:45]([O:8][CH:5]([CH3:6])[CH3:4])([OH:48])[CH:44]([C:49]([C:51]2[CH:52]=[C:53]([CH3:57])[CH:54]=[CH:55][CH:56]=2)=[CH2:50])[CH:43]=1

Participants

4

Reactant 3

HCID 21996962HCID 21996962, compound2×HCID 21996984HCID 21996984, compoundHCID 131722536HCID 131722536, compound

Product 1

HCID 70149291HCID 70149291, compound

Procedure

Employing the same general procedure as for the preparation of 4-bromo-1-isopropoxy-2-[(1-p-tolyl)vinyl]benzene (Compound S), 81.5 mg (0.3 mmol) of 4-bromo-2-[(1-m-tolyl)vinyl]phenol (Compound N) was converted into the title compound using 164 mg (0.6 mmol) of triphenylphosphine, 0.10 mL (108 mg, 0.6 mmol) of diethylazodicarboxylate, 0.05 mL (39 mg, 0.6 mmol) of isopropanol and 3 mL of tetrahydrofuran. The reaction was sluggish necessitating addition (after 23 hours of stirring at ambient temperature) of another equivalent of reagents (initially only 1/2 of the above amounts were added) and stirring for 4 additional days. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a pink oil.

Sources & evidence

ORD record
ord-b50355578ad843ebb669dcc4086c0b24
Source dataset
uspto-grants-2001_05
Patent number
US06225494B1

Reaction notes

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