Hexane → HCID 11567840, compound

HRID 735252Notes

Reaction equation

HRID 735252 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH3:29])[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([Cl:27])=[CH:21][C:22]=3[Cl:26])[NH:17][C:16]2=[O:28])=[CH:11][C:10]=1[Br:30])C1C=CC=CC=1.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[Br:30][C:10]1[CH:11]=[C:12]([C:15]2([CH3:29])[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([Cl:27])=[CH:21][C:22]=3[Cl:26])[NH:17][C:16]2=[O:28])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 11504338HCID 11504338, compound

Product 1

HCID 11567840HCID 11567840, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 3-(4-benzyloxy-3-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.10 g, 0.20 mmol) and BBr3 (0.59 mL, 1.0 M dichloromethane solution). After normal workup, the pure objective compound (65 mg, 78%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=2:1): 1H NMR (200 MHz, CDCl3) δ 1.70 (s, 3H, CH3), 5.51 (br s, 1H, OH), 6.76 (d, J=1.6 Hz, 1H, ArH), 6.94 (d, J=8.6 Hz, 1H, ArH), 7.02 (d, J=2 Hz, 1H, ArH), 7.28 (dd, J=8.6, 2.4 Hz, 1H, ArH); m.p. 228-229° C.; MS(EI) m/e 413 [M+], 381, 336, 299, 226; HRMS m/e cacld. for C16H10NO3Br1Cl2 412.9221, found 412.9195.

Workup

  1. customThe objective compound was prepared by the same procedure for the example 13

Sources & evidence

ORD record
ord-372ec6dd126f4a8b8a7068f4938a3833
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

Loading…