Hydrochloric Acid → 2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenol

HRID 1410294Notes

Reaction equation

HRID 1410294 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[O:19]C.Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[OH:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670691051-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzene

Product 1

HCID 711171942-Bromo-5-chloro-4-(4-ethoxybenzyl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzene (6, 11.3 mmol) in N,N-dimethylformamide (50 mL) was added sodium ethane thiolate (3.17 g, 34 mmol) and heated at 90° C. for 3 h. The reaction mixture was cooled to 0° C., neutralized with 1N HCl, and the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow oil which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33dd4c9da1e84a5db8d37e4334eb5bf6
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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