Cyclopentanol → 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

HRID 381391Notes

Reaction equation

HRID 381391 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[CH:11]1(O)[CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 1422285-Bromo-2-methoxyphenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-2-methoxyphenol (1 g), cyclopentanol (0.54 ml) and triphenylphosphine (1.55 g) in anhydrous tetrahydrofuran (20 ml), at 0° C., was treated with diethylazodicarboxylate (0.85 mi). The resulting yellow solution was stirred at 0° C. for 40 minutes then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (19:1, v/v) to give the title compound (1.2 g) as a pale yellow oil. NMR (CDCl3): δ1.62 (m,2H), 1.78-2.20 (m,6H), 3.79 (s,3H), 4.72 (m,1H), 6.70 (d,1H), 7.00 (dd,2H). Mass spectrum (FAB): m/z 270/272 (M)+.

Workup

  1. customthen evaporated
  2. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (19:1

Sources & evidence

ORD record
ord-5367dcb39e814514af43d81e6ef8267a
Source dataset
uspto-grants-2001_10
Patent number
US06306873B1

Reaction notes

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