Tetrahydrofuran toluene → HCID 71145282, compound

HRID 535328Notes

Reaction equation

HRID 535328 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:16][CH:15]3[S:17](=[O:19])(=[O:18])[CH:12]([CH2:13][CH2:14]3)[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:20][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:11][CH:12]3[S:17](=[O:19])(=[O:18])[CH:15]([CH2:14][CH2:13]3)[CH2:16]2)([OH:9])[CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 71145363HCID 71145363, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71145282HCID 71145282, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromo-phenyl)-(8,8-dioxo-8-thia-bicyclo[3.2.1]oct-3-yl)-methanone (885 mg, 2.58 mmol) in THF (7 ml) at −10° C. to −8° C. was added methylmagnesium bromide 1.4M in toluene/THF 3/1 (3.68 ml, 5.16 mmol). The reaction mixture was stirred for 30 min. The solution was cooled with an ice bath and quenched with a solution of aqueous saturated NH4Cl and water 1/1 (7.5 ml), diluted and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried using Na2SO4, filtered and concentrated in vacuo. The crude product (940 mg, 2.54 mmol, 97%) was used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled with an ice bath
  2. customquenched with a solution of aqueous saturated NH4Cl and water 1/1 (7.5 ml)
  3. additiondiluted
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c3693083c4748b298d073ed1623f13a
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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