Benzyl Bromide → 1-Benzyloxy-4-bromo-2-cyclopentyl-benzene

HRID 471947Notes

Reaction equation

HRID 471947 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 23090734HCID 23090734, compound

Product 1

HCID 593950681-Benzyloxy-4-bromo-2-cyclopentyl-benzeneYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-cyclopentyl-phenol (2.0 g, 8.29 mmol) and Cs2CO3 (3.24 g, 9.95 mmol) in DMF (13.0 mL) was added benzyl bromide (1.6 g, 1.09 mL, 9.12 mmol) dropwise. The reaction was stirred at room temperature under inert atmosphere for 2 h. The reaction was quenched with water and the aqueous layer was extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexane) provided 1-benzyloxy-4-bromo-2-cyclopentyl-benzene (1.8 g, 64% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.43-7.40 (m, 4H), 7.35-7.28 (m, 3H), 6.99 (d, J=9.4 Hz, 1H), 5.12 (s, 2H), 3.28-3.24 (m, 1H), 1.94-1.92 (m, 2H), 1.70-1.69 (m, 2H), 1.61-1.52 (m, 4H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8cdd0b7fde474bc685168f870319402b
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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