1-Bromo-4-fluorobenzene → HCID 11265628, compound

HRID 1792475Notes

Reaction equation

HRID 1792475 reaction equation
CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].Br[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.[Mg].[Cl-].[NH4+]>O1CCCC1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

Product 1

HCID 11265628HCID 11265628, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 2.32 g t-butyl N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate in tetrahydrofuran was added dropwise under ice-cooling to a tetrahydrofuran solution of Grignard reagent prepared from 5.2 g of 1-bromo-4-fluorobenzene and 1 g magnesium. The mixture was stirred at 5° C. for 2 hours, then poured into an aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The extract was purified by silica gel column, to give 2.6 g of t-butyl N-{(1S)-2-(4-fluorophenyl)-1-methyl-2-oxoethyl]carbamate as colorless oil. This product was treated with 4 N hydrochloric acid/ethyl acetate, to give 1.73 g of the title compound as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was purified by silica gel column

Sources & evidence

ORD record
ord-7d51ffea0f444886a4623476d3e4569f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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