Hydrochloric Acid → HCID 9863571, compound

HRID 722300Notes

Reaction equation

HRID 722300 reaction equation
[Br:1][C:2]1[C:11]2[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7][C:6]=2[CH:5]=[C:4]([Cl:21])[CH:3]=1.C(O)C.[OH-].[Na+].Cl>O.O1CCCC1>[Br:1][C:2]1[C:11]2[O:10][CH:9]([C:12]([F:14])([F:13])[F:15])[C:8]([C:16]([OH:18])=[O:17])=[CH:7][C:6]=2[CH:5]=[C:4]([Cl:21])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21883624HCID 21883624, compound

Product 1

HCID 9863571HCID 9863571, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-bromo-6-chloro-2-trifluoromethyl-2H-1-benzopyran-3-caboxylate (0.3 g), ethanol (15 mL), tetrahydrofuran (10 mL), and sodium hydroxide solution (10 mL, 2.5 N) were stirred at room temperature for 16 h. Hydrochloric acid (1 N) was added until the mixture was acidic to pH paper. The addition of water (50 mL) caused the formation of a precipitate which was collected by filtration yielding the title compound as a white solid (0.2 g, 72%): mp 227.8–228.9° C. 1H NMR (acetone-d6/300 MHz) 7.90 (s, 1H), 7.65 (dd, 2H, J=2.4 and J=28.8 Hz), 6.00 (qH-F, 1H, J=7.2 Hz). FABHRMS m/z 356.9134 (M+H, Calc'd 356.9141). Anal. Calc'd for C11H5BrClF3O3: C, 36.96; H, 1.41. Found: C, 37.05; H, 1.33.

Workup

  1. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a8c4352d8df94b58a91b29d63ed5eaf6
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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