Dichloromethane → HCID 77230927, compound

HRID 1466078Notes

Reaction equation

HRID 1466078 reaction equation
C(Cl)Cl.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][C:6]=1[O:15][CH3:16].[C:17](Cl)(=O)[C:18](Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3]>CN(C=O)C>[Br:4][C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][C:6]=1[O:15][CH3:16])[CH2:11][C:12](=[O:14])[CH2:18][CH2:17]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 27529944-Bromo-3-methoxybenzeneacetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 77230927HCID 77230927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DCM solution of (4-Bromo-3-methoxyphenyl)acetic acid (900 mg, 3.67 mmol) was added oxalyl chloride (0.64 ml, 7.3 mmol) and a drop of DMF. The solution was allowed to stir at RT for 3 hours, at which point bubbling stopped. The volatiles were removed under vacuum, and the residue was redissolved in DCM. The solution was cooled to 0° C. To this solution was added aluminum trichloride (1.2 g, 9.2 mmol). After stirring the mixture for 15 minutes, ethylene was bubbled into the reaction. The reaction was poured into ice, extracted with DCM, washed with brine, and purified by MPLC. LC-MS (IE, m/z): 255 [M+1]+.

Workup

  1. custombubbling
  2. customThe volatiles were removed under vacuum
  3. dissolutionthe residue was redissolved in DCM
  4. temperatureThe solution was cooled to 0° C
  5. stirringAfter stirring the mixture for 15 minutes
  6. customethylene was bubbled into the reaction
  7. additionThe reaction was poured into ice
  8. extractionextracted with DCM
  9. washwashed with brine
  10. custompurified by MPLC

Sources & evidence

ORD record
ord-59fc9c353a2a4edda23d8ef403db896d
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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