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

Triacetoxyperiodinane → 2'-Bromo-5'-isopropoxy-4'-methoxyacetophenone

HRID 41941
Notes
Print preview

Reaction equation

HRID 41941 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH:14]([OH:16])[CH3:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 667610431-(2-Bromo-5-isopropoxy-4-methoxyphenyl)ethanol

Product 1

HCID 667608062'-Bromo-5'-isopropoxy-4'-methoxyacetophenoneYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
18 °C

Procedure

A magnetically stirred solution of alcohol 37 (520 mg, 1.80 mmol) in CH2Cl2 (10 mL), maintained at 0° C. was treated with Dess-Martin periodinane (1.14 g, 2.69 mmol). The resulting mixture was warmed to 18° C., stirred at this temperature for 2 h then concentrated, under reduced pressure, onto TLC-grade silica (ca. 500 mg). The resulting free-flowing solid was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound 38 (361 mg, 70%) as a pale-yellow solid, m.p. 59.0-59.9° C., Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Workup

  1. concentrationthen concentrated, under reduced pressure, onto TLC-grade silica (ca. 500 mg)
  2. washThe resulting free-flowing solid was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-9e37fec69edb48d4848ac77cbe79f665
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536157B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes