Ammonium Chloride → HCID 15550692, compound

HRID 489478Notes

Reaction equation

HRID 489478 reaction equation
[CH2:1]([Li])CCC.[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[CH2:16][O:15]1.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17]([C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)=[CH2:1])[CH2:16][O:15]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 17892881HCID 17892881, compoundHCID 178418339Butyllithium

Product 1

HCID 15550692HCID 15550692, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

n-Butyllithium (50 ml, 2.5 M in hexane, 125 mmol) was added dropwise over 10 minutes to a stirred suspension of methyltriphenylphosphonium bromide (45.0 g, 126 mmol) in dry THF (600 ml) under nitrogen at −70° C. The mixture was allowed to warm to −20° C., over 20 minutes, then a solution of 2-(2,4-difluorophenyl)-2-(4-iodobenzoyl)oxirane [37.46 g, 97 mmol, from step (d)] in dry THF (200 ml) was added over 5 minutes. The mixture was allowed to warm to room temperature and stirred for 84 hours. 10% Aqueous ammonium chloride (500 ml) was added, and the mixture was concentrated under reduced pressure. The product was extracted into ethyl acetate and the combined extracts were dried (MgSO4) and concentrated under reduced pressure. The solid residue was treated with boiling hexane (3×500 ml), and the residual solid discarded. The hexane solutions were combined, filtered through a short pad of silica gel, and concentrated under reduced pressure to give the title compound as a yellow oil (34.3 g, 92%), which was characterised by 1H-N.M.R. spectroscopy.

Workup

  1. temperatureto warm to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. additionThe solid residue was treated with boiling hexane (3×500 ml)
  7. filtrationfiltered through a short pad of silica gel
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-971a0a31807440ae8c04309ae3afad07
Source dataset
uspto-grants-2005_12
Patent number
US06977302B2

Reaction notes

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