Hydrochloric Acid → 2-(Allyloxy(4-ethoxyphenyl)methyl)-4-bromo-1-chlorobenzene

HRID 625841Notes

Reaction equation

HRID 625841 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.O1C[CH2:23][CH2:22][CH2:21]1.[H-].[Na+].[H][H].C(Br)C=C.Cl>C(OCC)(=O)C>[CH2:23]([O:9][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)[C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:19])[CH:22]=[CH2:21]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 61100046(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 671540412-(Allyloxy(4-ethoxyphenyl)methyl)-4-bromo-1-chlorobenzeneYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suitable reaction flask was charged (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanol (2.93 mmoles; 1.00 g) and tetrahydrofuran (122.89 mmoles; 10.00 mL; 8.86 g) to afford a clear solution. Sodium hydride (8.14 mmoles; 325.61 mg) was then added in small portions to minimize the rate of hydrogen gas evolution. The reaction was stirred for approximately 30 minutes at room temperature, and then allyl bromide (8.55 mmoles; 0.740 mL; 1.03 g) was added slowly. The reaction was allowed to stir at room temperature until completion (as determined by GCMS analysis). To the reaction mixture was then added 1N hydrochloric acid (10 mL) and ethyl acetate (20 mL). The layers were shaken together, allowed to settle and then were separated. The organic phase was washed with saturated aqueous sodium chloride (10 mL) and then was dried over magnesium sulfate, filtered and concentrated to provide the crude product (1.07 g). The crude oil was purified by flash chromatography on silica gel eluting with a gradient of 0 to 5% ethyl acetate in hexanes to afford 858 mg of product as a clear oil (77% yield).

Workup

  1. customto afford a clear solution
  2. stirringto stir at room temperature until completion (as determined by GCMS analysis)
  3. stirringThe layers were shaken together
  4. customwere separated
  5. washThe organic phase was washed with saturated aqueous sodium chloride (10 mL)
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto provide the crude product (1.07 g)
  10. customThe crude oil was purified by flash chromatography on silica gel eluting with a gradient of 0 to 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3f93903ee0144d62800b6ae05e7eaeb6
Source dataset
uspto-grants-2016_04
Patent number
US09308204B2

Reaction notes

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