Benzene, 1-bromo-3,5-dichloro- → HCID 2758146, compound

HRID 924937

Reaction equation

HRID 924937 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[CH:3]=1.[Li]CCCC.C1([C:21](=[O:30])[CH2:22][C:23]2[CH:24]=[C:25](C)[CH:26]=[CH:27][CH:28]=2)C=CC=CC=1>C1COCC1>[Cl:9][C:4]1[CH:3]=[C:2]([C:21](=[O:30])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:7]=[C:6]([Cl:8])[CH:5]=1

Participants

5

Reactant 3

HCID 29766Benzene, 1-bromo-3,5-dichloro-HCID 131736142-(3-Methylphenyl)-1-phenylethan-1-one2×HCID 178418339Butyllithium

Product 1

HCID 2758146HCID 2758146, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-3,5-dichlorobenzene (1 g, 4.4 mmol) in anhydrous THF (10 mL) was added n-BuLi (339 mg, 5.3 mmol) at −78° C. After being stirred for 30 minutes, a solution of N-methoxy-N-methyl-2-phenyl-acetamide (prepared following step 1 of Intermediate 4) (790 mg, 4.4 mmol) in THF (5 mL) was added, and the mixture was stirred for 3 hours. When TLC indicated that starting material was consumed, the reaction mixture was diluted with water (50 mL), and extracted with EtOAc (20 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuum, and purified by column chromatography (PE:EtOAc=50:1) to afford 1-(3,5-dichlorophenyl)-2-phenylethanone (213 mg, yield 19.4%).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customwas consumed
  3. additionthe reaction mixture was diluted with water (50 mL)
  4. extractionextracted with EtOAc (20 mL×3)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuum
  7. custompurified by column chromatography (PE:EtOAc=50:1)

Sources & evidence

ORD record
ord-f583a15e0ab34369ac2424830551738d
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Linked notes

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