Chloroacetyl chloride → 3-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

HRID 1108403Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH:14])[CH:8]=1)[CH3:2].C([O-])(O)=O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:23](=[O:24])[CH2:22][Cl:21])=[C:9]([OH:14])[CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 11-3 (3.38 g, 16.3 mmol) in CHCl3 (80 mL) was added saturated NaHCO3 (50 mL) and it was then chilled to 0° C. A solution of chloroacetyl chloride (1.94 mL, 24.4 mmol) in CHCl3 (30 mL) was added dropwise to the chilled biphase. Upon addition completion, the reaction was stirred at 0° C. for 1 h. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give 11-4 which was used without further purification in the next step.

Workup

additionUpon addition completion
customThe layers were separated
extractionthe aqueous layer was extracted twice with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customto give 11-4 which
customwas used without further purification in the next step

Sources & evidence

ORD record: ord-dd324a62acf3461f91b57b8eb64d2328
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066648

Reaction notes

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