Diethyl Ether → HCID 67241231, compound

HRID 1970299Notes

Reaction equation

HRID 1970299 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH:8]=[C:9]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:10]([F:17])=[CH:11][C:12]=3[C:13]2=O)=[CH:4][CH:3]=1.[CH3:24][Mg]Br.C(OCC)C.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH:8]=[C:9]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])[C:10]([F:17])=[CH:11][C:12]=3[C:13]2=[CH2:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 67241298HCID 67241298, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67241231HCID 67241231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-2-fluoro-3-(2,2,2-trifluoroethoxy)-9H-xanthen-9-one (2.00 g, 5.11 mmol) in THF (25 mL) at 0° C. was added methylmagnesium bromide 3.0 M in diethyl ether (3.41 mL, 10.23 mmol) slowly. After addition, the mixture was stirred at room temperature for overnight. Then, the mixture was cooled to 0° C. and saturated ammonium chloride (50 mL) was added slowly. The mixture was then stirred at RT for 15 min. Then, the organic layer was collected and the aqueous layer was extracted with EtOAc (1×50 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give 7-bromo-2-fluoro-9-methylene-3-(2,2,2-trifluoroethoxy)-9H-xanthene as a brown solid. MS (ESI, positive ion) m/z: 388.9, 390.9 (M+1).

Workup

  1. additionAfter addition
  2. temperatureThen, the mixture was cooled to 0° C.
  3. stirringThe mixture was then stirred at RT for 15 min
  4. customThen, the organic layer was collected
  5. extractionthe aqueous layer was extracted with EtOAc (1×50 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d213fff7704b4eb588f94170b01506e1
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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