3-Bromobenzene-1-sulfonyl fluoride → Benzene, 1-bromo-3-(phenylsulfonyl)-

HRID 855512Notes

Reaction equation

HRID 855512 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](F)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:12]1([S:8]([C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 707000393-Bromobenzene-1-sulfonyl fluorideHCID 178418255HCID 178418255, compound

Product 1

HCID 640920Benzene, 1-bromo-3-(phenylsulfonyl)-Yield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-bromophenylsulfonyl fluoride (D1) (1 g, 4.18 mmol) in dry THF (20 ml) at −78° C., under argon was added phenylmagnesium bromide (1M, 1.4 ml, 4.18 mmol) dropwise. The reaction was left to warm to room temperature overnight and then quenched with ammonium chloride (50 ml), extracted with ethyl acetate (3×40 ml) and the combined organic extracts dried (Na2SO4). Solvents were evaporated in vacuo to give a colourless solid (1.09 g, 88%).

Workup

  1. waitThe reaction was left
  2. customquenched with ammonium chloride (50 ml)
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-aaeb9621657b45e89bde9f8c40fcda06
Source dataset
uspto-grants-2007_08
Patent number
US07262188B2

Reaction notes

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