Water → ethyl 8-chloro-6-ethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854990

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:28](B(CC)CC)[CH3:29].O>CN(C=O)C.C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:28][CH3:29])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 500 mg (1.16 mmol) ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 3 mL of anhydrous DMF was added 0.481 g (3.48 mmol, 3.0 eq.) of potassium carbonate, 0.134 g (0.116 mmol, 0.1 eq.) of tetrakis(triphenylphosphine)-palladium(0) and 1.74 mL (1.74 mmol, 1.5 eq.) of 1M triethylborane in THF. The vessel was heated to 110° C. for 5 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic layer was washed 4 times with water and 2 times with brine, dried over sodium sulfate, filtered and concd in vacuo. The product was carried to the next step without further purification.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed 4 times with water and 2 times with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customThe product was carried to the next step without further purification

Sources & evidence

ORD record: ord-35a02430a678469aa529f4c8dd031065
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Linked notes

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