Ethyl Acetate → HCID 86618286, compound

HRID 2264575Notes

Reaction equation

HRID 2264575 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:30])([F:29])[C:7]1[CH:8]=[C:9]([NH:13][C:14]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[C:24]([O:27]C)[CH:25]=[CH:26][C:17]2=3)=[O:15])[CH:10]=[CH:11][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C(Cl)Cl.C(=O)=O.CC(C)=O>[F:29][C:6]([F:5])([F:30])[C:7]1[CH:8]=[C:9]([NH:13][C:14]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:17]2=3)=[O:15])[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 86618287HCID 86618287, compound

Product 1

HCID 86618286HCID 86618286, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-42.5 °C

Procedure

A solution of 10 ml BBr3 in 40 ml CH2Cl2 is cooled in dry ice and acetone. Then 2.43 g (6.67 mMol) of 7-methoxy-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide in 20 ml CH2Cl2 are added dropwise. The mixture is warmed up (−45 to −40° C.) and then stirred at this temperature for 1.5 h. The solution is poured into a mixture of 300 g ice, 150 ml sat. Na2CO3 solution and 200 ml EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water (2×) and brine, dried (Na2SO4) and concentrated. Crystallization from hexane gives the title compound: m.p.: 172-173° C.; MS: [M+1]+=351; Anal.: C,H,N,F.

Workup

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallization from hexane

Sources & evidence

ORD record
ord-2392eeb6098b4ce1ad70faabd872b7cd
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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