Allyl bromide → HCID 86729318, compound

HRID 1474617Notes

Reaction equation

HRID 1474617 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:23](Br)[CH:24]=[CH2:25]>CN(C=O)C.C(OCC)(=O)C>[CH2:25]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]2[CH:15]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:16])=[CH:9][CH:10]=1)[CH:24]=[CH2:23]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol

Product 1

HCID 86729318HCID 86729318, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-bromo-2-chlorobenzyl)phenol (6 g, 20.16 mmol, prepared as described in WO2006120208) in dry DMF (25 mL), was added Cs2CO3 (18.2 g, 60.6 mmol) and allyl bromide (4.2 mL, 50.6 mmol) at 0° C. and the reaction mixture was stirred at r.t. for 2 h. After the completion of the reaction as monitored by TLC, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with water (3×30 mL). The combined organic layers were dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 0.4:9.6 Ethyl acetate:Pet. Ether) to afford the title compound (6.1 g, 89.6%).

Workup

  1. customAfter the completion of the reaction
  2. washwashed with water (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 0.4:9.6 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-8f32f61a2d274507b1e85c271ed6c6bf
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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