N-bromobutanimide → ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854977Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.[Br:22]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1>[Br:22][CH2:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]([C:13]([F:16])([F:15])[F:14])[O:8]2)=[CH:3][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 84 °C

Procedure

To a mixture of the product of Example 157 Step 2 (4.0 g, 12.5 mmol), N-bromosuccinimide (2.3 g, 13.1 mmol), and 21 mL benzene, was added benzoyl peroxide (145 mg. 0.6 mmol). The reaction was heated to 84° C. After 5 h, the reaction was cooled to 25° C. and stored overnight. Solid was removed from the reaction by filtration, and washed with 4 mL benzene. To the filtrate, was added N-bromosuccinimide (1.0 g, 5.7 mmol) and benzoyl peroxide (145 mg, 0.6 mmol). The reaction was heated to 84° C. After 2.5 h, the reaction was cooled to 25° C. The solid was removed from the reaction by filtration and the filtrate was concentrated. The residue was purified by flash chromatography (toluene/EtOAc=9/1) to give 3.9 g a yellow solid of reasonably pure material, which was used without further purification.

Workup

temperaturethe reaction was cooled to 25° C.
waitstored overnight
customSolid was removed from the reaction by filtration
washwashed with 4 mL benzene
temperatureThe reaction was heated to 84° C
waitAfter 2.5 h
temperaturethe reaction was cooled to 25° C
customThe solid was removed from the reaction by filtration
concentrationthe filtrate was concentrated
customThe residue was purified by flash chromatography (toluene/EtOAc=9/1)

Sources & evidence

ORD record: ord-c1e21781007344f2aee7651daa9e94ed
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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