Bromine → HCID 18322217, compound

HRID 1698843Notes

Reaction equation

[Mg].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.BrBr.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])[CH:20]=[CH:21][CH:22]=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[OH:30][C:29]1([C:7]2[CH:8]=[CH:9][C:4]([C:3]([F:12])([F:11])[F:2])=[CH:5][CH:6]=2)[C:28]2[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26](=[O:35])[N:25]1[CH2:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH3:15])[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At room temperature, 172 mg (7.08 mmol) of magnesium turnings in 10 ml of absolute diethyl ether were admixed with 1.6 g (7.11 mmol) of 4-trifluoromethylbromobenzene. The reaction was started by addition of a drop of bromine. After about 2 h, the magnesium had completely dissolved. The mixture was cooled to 0° C. and 0.5 g (1.78 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide was added. The reaction mixture was allowed to warm to room temperature and, after 2 h, admixed with 5 ml of saturated sodium bicarbonate solution. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried and evaporated to dryness using a rotary evaporator. The red crystalline residue was recrystallized from toluene. This gave a colorless product. Yield: 0.49 g. M.p.: 167° C.

Workup

customAt room temperature
temperatureto warm to room temperature and, after 2 h
extractionThe aqueous phase was extracted twice with diethyl ether
customThe combined organic phases were dried
customevaporated to dryness
customa rotary evaporator
customThe red crystalline residue was recrystallized from toluene
customThis gave a colorless product

Sources & evidence

ORD record: ord-60e99fabdeb648f18889d88111753765
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344468B1

Reaction notes

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