Hydrochloric Acid → HCID 59456309, compound

HRID 1873441Notes

Reaction equation

[Li]N1C(C)(C)CCCC1(C)C.[Li]CCCC.[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[Te:27][CH:28]=[CH:29][CH:30]=2)=[C:22]([F:31])[C:21]=1[F:32])[CH3:18].[CH:33](N1CCOCC1)=[O:34].Cl>C1COCC1.O>[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[Te:27][C:28]([CH:33]=[O:34])=[CH:29][CH:30]=2)=[C:22]([F:31])[C:21]=1[F:32])[CH3:18]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of LiTMP (comprising 3.9 ml (22.9 mmol) of TMP and 14.0 ml (22.3 mmol, 15% soln. in hexane) of n-BuLi) is added to 6.8 g (20.3 mmol) of 2-(4-ethoxy-2,3-difluorophenyl)tellurophene in 70 ml of THF at 0° C. The mixture is stirred at this temperature for 1 h. The solution is cooled to −60° C., and N-formylmorpholine is added. The reaction mixture is warmed to 0° C. and stirred for 1 h. Water and 2 N hydrochloric acid are added, and the mixture is extracted with MTBE. The organic phase is washed with sodium chloride and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is recrystallised from toluene. Drying in vacuo gives 5-(4-ethoxy-2,3-difluorophenyl)tellurophene-2-carbaldehyde as a brown solid.

Workup

temperatureThe reaction mixture is warmed to 0° C.
stirringstirred for 1 h
extractionthe mixture is extracted with MTBE
washThe organic phase is washed with sodium chloride
customdried
concentrationThe solution is concentrated to dryness
customthe residue is recrystallised from toluene
customDrying in vacuo

Sources & evidence

ORD record: ord-fde3f3cd3e2f443e8cc4cba73c71aeb2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304036B2

Reaction notes

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