6-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE → HCID 18410349, compound

HRID 993353Notes

Reaction equation

HRID 993353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH2:14]Cl.BrC1C=C2C(=CC=1O)[O:23][C:22](=[O:28])[CH:21]=C2CCl>>[C:22]([O:28][CH2:14][C:5]1[C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=2)[O:8][C:7](=[O:13])[CH:6]=1)(=[O:23])[CH3:21]

Participants

3

Reactant 2

HCID 54239766-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONEHCID 184103446-Bromo-4-(chloromethyl)-7-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 18410349HCID 18410349, compoundYield 28%

Procedure

This compound was prepared by the same method as compound 5, starting with compound 12 rather than compound 11, to yield 75.4 mg (0.281 mmol, 28% yield) of compound 4 as an oil. 1H NMR (CDCl3+5% CD3OD) δ 7.43 (1H, s), 6.85 (1H, s), 6.25 (1H, s), 5.16 (2H, s), 3.30 (1H, s), 2.14 (3H, s); MS (ES, negative) 267.2 and 269.1; UV (KMOPS, pH 7.2) λmax (ε) 370 nm (16,000 M−1cm−1). ps 3,6,8-Tribromo-4-chloromethyl-7-hydroxycoumarin (13).

Workup

  1. customThis compound was prepared by the same method as compound 5

Sources & evidence

ORD record
ord-5323cd566c3f4acf885aa8d3686b2616
Source dataset
uspto-grants-2002_10
Patent number
US06472541B2

Reaction notes

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