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Oxalyl chloride → (2-Bromo-5-methoxy-4-methyl-phenyl)-acetic acid chloride

HRID 1691781
Notes
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Reaction equation

HRID 1691781 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=O.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][C:12]([Cl:18])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 291672(2-Bromo-5-methoxy-4-methylphenyl)acetic acid

Product 1

HCID 59377714(2-Bromo-5-methoxy-4-methyl-phenyl)-acetic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-5-methoxy-4-methyl-phenyl)-acetic acid (149.4 mg) in dichloromethane (1.8 mL) was added oxalyl chloride (0.055 mL) followed by DMF (1 drop) uder argon. Mixture was stirred at rt for 3 h. Mixture was concentrated to dryness. Dichloroethane (ca. 10 mL) was added, and the mixture was back concentrated to dryness to obtain crude (2-bromo-5-methoxy-4-methyl-phenyl)-acetic acid chloride (151 mg).

Workup

  1. concentrationMixture was concentrated to dryness
  2. additionDichloroethane (ca. 10 mL) was added
  3. concentrationthe mixture was back concentrated to dryness

Sources & evidence

ORD record
ord-ac473a77240f48d9a5d40899e3546efe
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153808B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes