4-Bromotoluene → HCID 24800455, compound

HRID 1417748Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1[O:25][CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([Li])CCC>>[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]([OH:22])[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:19][C:18]=1[O:25][CH3:26])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 78054-Bromotoluene

HCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

HCID 178418339Butyllithium

Product 1

HCID 24800455HCID 24800455, compound

Procedure

The synthesis is based essentially on the reaction of 4-bromotoluene with 4-(benzyloxy)-3-methoxybenzaldehyde in the presence of butyllithium to give 4-(benzyloxy)-3-methoxy-4'-methylbenzhydrol. By oxidation to 4-(benzyloxy)-3-methoxy-4'-methylbenzophenone and subsequent debenzylation there is obtained 4-hydroxy-3-methoxy-4'-methylbenzophenone. After regioselective nitration to 4-hydroxy-3-methoxy-4'-methyl-5-nitrobenzophenone and subsequent hydrolysis of the methoxy group there is obtained the aforementioned inhibitor 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone.

Sources & evidence

ORD record: ord-4335ebbf60a04adbade49576eeacbf2c
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877353

Reaction notes

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