Azobisisobutyronitrile → HCID 58758947, compound

HRID 2374652Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[OH:21][C:22]([CH3:45])([CH3:44])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38](=[O:43])[C:39]([OH:42])([CH3:41])[CH3:40])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=[O:24]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:31]([C:28]1[CH:27]=[CH:26][C:25]([C:23](=[O:24])[C:22]([OH:21])([CH3:45])[CH3:44])=[CH:30][CH:29]=1)[C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:43])[C:39]([OH:42])([CH3:41])[CH3:40])=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 40 °C

Procedure

11.2 g (0.063 mol) N-bromosuccinimide, and 0.12 g AIBN (2,2-azobis(2-methylpropionitrile)) were suspended in 50 ml carbon tetrachloride and heated to 40° C. under argon. Then a solution of 20.45 g (0.06 mol) of 2-Hydroxy-1{-4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}2-methyl-propan-1-one (known from PCT Int. Appl. WO 2003040076) in 50 ml carbon tetrachloride was added dropwise over 15 min. After stirring at 75° C. for 3 h, the reaction mixture was cooled to 25° C., filtered, and washed neutral with water, dried over magnesium sulfate and concentrated by evaporation. The raw product (28.4 g) was a brownish resin that was pure enough for further derivatization of the benzylic bromide. The structure was confirmed by 1H-NMR (CDCl3): δ [ppm]: 8.04 (d, 4H), 7.53 (d, 4H), 6.28 (s, 1H, benzylic), 3.95, (s, 2H, OH), 1.61 (s, 12H),

Workup

temperaturethe reaction mixture was cooled to 25° C.
filtrationfiltered
washwashed neutral with water
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-8eaaaedf88ec409b948017a65acfe812
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462650B2

Reaction notes

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