4-Bromobenzoyl chloride → 1-(4-Bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanone

HRID 1597578Notes

Reaction equation

HRID 1597578 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[C:15]([F:21])[CH:14]=1>COCCOC.[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[C:15]([F:21])[CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 223168194-(Bromomethyl)-2-fluoro-1-(methylsulfanyl)benzene

Product 1

HCID 223166761-(4-Bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanoneYield 73%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To the mixture of 4-bromobenzoyl chloride (10.81 g, 49.26 mmol), zinc (4.40 g, 67.24 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.99 g, 2.586 mmol in DME (250 mL) was added dropwise the solution of 4-(bromomethyl)-2-fluoro-1-(methylsulfanyl)benzene (12.16 g, 51.72 mmol) in DME (120 mL) at room temperature. After 2.5 hour, the mixture was filtered through celite, the filtrate was evaporated, diluted with ethyl acetate (300 mL), washed with water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue was washed with ethyl acetate-isopropylether, to give the subtitle compound (12.16 g, 73% yield) as a solid.

Workup

  1. filtrationthe mixture was filtered through celite
  2. customthe filtrate was evaporated
  3. additiondiluted with ethyl acetate (300 mL)
  4. washwashed with water (100 mL), brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-792b8593a7f0404b85885f0d0fc4b2bb
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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