HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl Ester → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

HRID 858573
Notes
Print preview

Reaction equation

HRID 858573 reaction equation
N1C=CC=CC=1S[C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[Cl:16].[CH3:18][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([C:8](=[O:17])[CH3:18])=[C:10]([Cl:16])[CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 210622544-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl EsterHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, compound

Product 1

HCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl ester (1.86 g, 5.66 mmol) from Step 1 above was dissolved in dry THF (30 mL) and cooled to −78° C. A solution of methyl magnesium bromide in 75:25 toluene/THF (1.4 M, 4.45 mL, 6.23 mmol) was added dropwise. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated 1N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (1.05 g, 80%) as a colorless oil.

Workup

  1. customthe cooling bath was removed
  2. customThe reaction mixture was quenched with saturated 1N HCl
  3. extractionextracted with EtOAc (30 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6e62ab795fa049dea8512350ba432d66
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07148226B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes