1-Bromo-2-fluorobenzene → HCID 69416906, compound

HRID 1593355Notes

Reaction equation

HRID 1593355 reaction equation
C(N(CC)[C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[CH:6]=1)C.Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:18]=1[F:26].BrC1C=CC=CC=1F.[Li+].CC([N-]C(C)C)C.BrC1C(F)=C(C=CC=1)C=O.CC(C)([O-])C.[K+].BrC1C=CC=C(F)C=1F>C1COCC1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C(O)C.[Pt]=O.CN(C=O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][C:22]3[C:17]([C:6]=2[C:7]=1[F:12])=[C:18]([F:26])[C:19]([CH2:23][CH2:24][CH3:25])=[CH:20][CH:21]=3

Participants

13

Reactant 7

HCID 612591-Bromo-2-fluorobenzeneHCID 2724682Lithium diisopropylamideHCID 27332601-Bromo-2,3-difluorobenzeneHCID 17683062HCID 17683062, compoundHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 69415164HCID 69415164, compound

Product 1

HCID 69416906HCID 69416906, compound

Reagents, catalysts & solvents 5

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to example 1, but using N,N-diethyl-3,4-difluorobenzamide (prepared from purchasable 3,4-difluorobenzoic acid [455-86-7] by successive reaction with thionyl chloride and diethylamine) instead of N,N-diethyl-4-n-propylbenzamide and 1-bromo-2-fluoro-3-propylbenzene (prepared from 1-bromo-2-fluorobenzene by lithiation with LDA in THF at −70° C. and subsequent reaction with DMF, Wittig reaction of the resulting 3-bromo-2-fluorobenzaldehyde with ethyltriphenylphosphonium bromide and potassium tert-butoxide in THF and hydrogenation with platinum oxide in ethanol) instead of 1-bromo-2,3-difluorobenzene, 3,4,5-trifluoro-6-propylfluorene is obtained.

Workup

  1. customsubsequent reaction

Sources & evidence

ORD record
ord-2891797314f441a582f58cd5ce209cf4
Source dataset
uspto-grants-2007_11
Patent number
US07297379B2

Reaction notes

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