Allyl bromide → 4-(Phenylmethoxy)-2-(2-propen-1-yl)-1-(2-propen-1-yloxy)benzene

HRID 898458Notes

Reaction equation

HRID 898458 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])[CH:2]=[CH2:3].[CH2:19](Br)[CH:20]=[CH2:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(C(C)=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:18][CH2:21][CH:20]=[CH2:19])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 18701949HCID 18701949, compound

Product 1

HCID 222611304-(Phenylmethoxy)-2-(2-propen-1-yl)-1-(2-propen-1-yloxy)benzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-allyl-4-benzyloxy-phenol (ER2-YYR-17) (35.56 g, 148 mmol), allyl bromide (21.5 g, 178 mmol), cesium carbonate (58 g, 178 mmol) and methyl ethyl ketone (400 mL) was refluxed with stirring in a 1 L round bottomed flask. After 23 h, the reaction was cooled and concentrated. The residue was partitioned between water (500 mL) and EtOAc (400 mL). The organic layer was dried (MgSO4) and concentrated to a tan oil, 39.37 (95%) ER0-LKW-190A: 1H NMR (CDCl3) δ 3.45 (dd, 2H), 4.54 (dd, 2H), 5.04 (s, 2H), 5.18 (m, 2H), 5.29 (dd, 1H), 5.46 (dd, 1H), 5.94-6.18 (m, 2H), 6.81 (s, 2H), 6.88 (s, 1H), 7.30-7.48 (m, 5H), MS (ES) m/e 281 [M+1].

Workup

  1. temperaturewas refluxed
  2. temperaturethe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between water (500 mL) and EtOAc (400 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated to a tan oil, 39.37 (95%)

Sources & evidence

ORD record
ord-dd18b56d31a045fd98dbd5d441db7e2a
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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