Ammonium Chloride → HCID 68451303, compound

HRID 658095Notes

Reaction equation

[CH2:1]([Li])CCC.C1COCC1.[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:32][C:33]1[C:45]([CH:46]=O)=[C:44]([F:48])[CH:43]=[CH:42][C:34]=1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[Cl-].[NH4+]>C1COCC1>[F:32][C:33]1[C:45]([CH:46]=[CH2:1])=[C:44]([F:48])[CH:43]=[CH:42][C:34]=1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

At −78° C., 9.50 ml of 1.59 M n-butyl lithium-THF solution was added dropwise to 90 ml of THF solution containing 8.13 g of methyltriphenylphosphonium iodide. This was stirred at 0° C. for 10 minutes, cooled to −78° C. and then mixed with 2.44 g of tert-butyl 2,4-difluoro-3-formylbenzoate dissolved in 10 ml of THF. After 40 minutes thereof, this was stirred at room temperature for 1 hour, mixed with appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and then dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 1.20 g (50%) of tert-butyl 2,4-difluoro-3-vinylbenzoate (Reference Example 5-1) from a hexane-ethyl acetate (50:1) eluate. ES−: 239

Workup

temperaturecooled to −78° C.
waitAfter 40 minutes
stirringthis was stirred at room temperature for 1 hour
custompurified water
extractionextracted with ethyl acetate
dry with materialdried with anhydrous magnesium sulfate
concentrationAfter concentration
customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-d3424850e7084df9b99bb89841dd8669
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076367B2

Reaction notes

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