Water → 1-Allyloxy-2-bromo-4-trifluoromethoxy-benzene

HRID 1420809Notes

Reaction equation

HRID 1420809 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][CH2:22][CH:21]=[CH2:20]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 187824911-Allyloxy-2-bromo-4-trifluoromethoxy-benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-4-trifluoromethoxyphenol (Description 11; 8 g, 0.03 mol) and K2CO3 (8.6 g, 0.06 mol) in dimethylformamide (100 ml) was added allyl bromide (4 ml, 0.045 mol). The solution was stirred for 4 h. at room temperature undre nitrogen whereupon water (400 ml) and ethyl acetate (3×100 ml) were added and the combined organic phase was washed with water (200 ml), saturated brine (200 ml), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography on silica gel (eluting with 5% ethyl acetate in hexane) to give the title compound as a yellow oil 1H NMR (250 MHz, CDCl3) δ4.60 (2H, dt, J 5, 1.6 Hz), 5.33 (1H, dq, J 10.5, 1.4 Hz), 5.48 (1H, dq, J 17.3, 1.6 Hz), 6.04 (1H, m), 6.86 (1H, d, J 9 Hz, 7.13 (1H, dd, J 8.4, 2.7 Hz), and 7.45 (1H, d, J 2.8 Hz).

Workup

  1. additionwere added
  2. washthe combined organic phase was washed with water (200 ml), saturated brine (200 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by chromatography on silica gel (eluting with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c0dc39a43ba6403a852b6cebe9d918ef
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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