Water → 1-Chloro-2-ethynyl-3-fluorobenzene

HRID 2368501Notes

Reaction equation

HRID 2368501 reaction equation
[Br-].Br[CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[Cl:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:31]=1[CH:32]=O.O>C1COCC1>[Cl:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:31]=1[C:32]#[CH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 678472-Chloro-6-fluorobenzaldehydeHCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxide

Product 1

HCID 570100721-Chloro-2-ethynyl-3-fluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of (bromomethyl)triphenylphosphonium bromide (3.3 g, 7.6 mmol) in THF at 0° C. was added potassium tert-butoxide (2.12 g, 18.9 mmol). The reaction was stirred for 30 minutes and a solution of 2-chloro-6-fluorobenzaldehyde (1 g, 6.31 mmol) in THF was added. The reaction was allowed to warm to room temperature overnight and water was added. The solution was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-10% EtOAc in hexanes) to give 1-chloro-2-ethynyl-3-fluorobenzene (41).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9571faa41c314666bb371e1e1d293ecd
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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