Potassium tert-butoxide → 2-{2-Chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane

HRID 2046644Notes

Reaction equation

HRID 2046644 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[Cl:7][C:8]1[C:15]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)=[CH:14][CH:13]=[C:12]([F:21])[C:9]=1[CH:10]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.[Cl-].[Na+].O>[Cl:7][C:8]1[C:9]([CH:10]=[CH:1][CH3:2])=[C:12]([F:21])[CH:13]=[CH:14][C:15]=1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1

Participants

6

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 593705312-Chloro-3-(1,3-dioxolan-2-yl)-6-fluorobenzaldehyde

Product 1

HCID 686033642-{2-Chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolaneYield 99.3%

Reagents, catalysts & solvents 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyltriphenylphosphonium bromide (3.43 g) in tetrahydrofuran (15 mL) was added potassium tert-butoxide (1.31 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Successively, 2-chloro-3-(1,3-dioxolan-2-yl)-6-fluorobenzaldehyde (1.35 g) was added to the mixture, and the mixture was stirred for 2.5 hr. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude 2-{2-chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane (1.41 g).

Workup

  1. stirringthe mixture was stirred for 2.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-463dbc2f9daa41daaa87b48956d18432
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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