1,4-Dibromobutane → Methyl 3-chloro-4-(4-bromobutyloxy)-phenylacetate

HRID 342779Notes

Reaction equation

HRID 342779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>CO.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:18][CH2:17][CH2:16][CH2:15][Br:14]

Participants

7

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 92625Methyl 3-chloro-4-hydroxyphenylacetate

Product 1

HCID 15290476Methyl 3-chloro-4-(4-bromobutyloxy)-phenylacetate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-chloro-4-hydroxyphenylacetate and 1,4-dibromobutane (0.021 g, 0.044 mmol) in 0.5 mL of methanol was added 5N NaOH soln (0.04 mL, 5 eq) at rt. The reaction mixture was heated initially with a heat gun to reflux in order to dissolve the starting material. After heating, the reaction mixture stirred at ambient temperature for 1 h. The reaction mixture was diluted with EtOAc and 0.1N HCl (5 mL). The organic layer was separated from the aqueous portion, and washed with 0.1N HCl (5 mL) followed by 10 mL brine. The organic layer was dried (MgSO4), filtered, and evaporated in vacuo to afford the title compound. This compound was taken forward without further purification.

Workup

  1. temperatureThe reaction mixture was heated initially with a heat gun
  2. temperatureto reflux in order
  3. dissolutionto dissolve the starting material
  4. temperatureAfter heating
  5. customThe organic layer was separated from the aqueous portion
  6. washwashed with 0.1N HCl (5 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-64679126521a479a8f532e7a72535a5c
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

Loading…