Boron tribromide → HCID 11152159, compound

HRID 2100176Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[C:18]2[CH2:19][C:20]([CH3:27])([CH3:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH2:23]2)[C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 68654575HCID 68654575, compound

Product 1

HCID 11152159HCID 11152159, compoundYield 52%

Procedure

The demethylation protocol described for 208 was used. 4-[[4-(methyloxy)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]benzonitrile (209) (0.700 g, 1.95 mmol) was treated with BBr3 to afford 0.350 g (52%) of compound 210 as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, J=8.1 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.02.(d, J=8.4 Hz, 2H), 6.79 (d, J=8.7 Hz, 2H), 2.01 (s, 2H), 1.94 (s, 2H), 1.33 (s, 2H), 0.96 (s, 6H), 0.95 (s, 6H). LCMS (ESI): m/z 344 (M−H)−.

Sources & evidence

ORD record: ord-8fc37f588a5040c4bfd6b7d723873ac4
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569601B2

Reaction notes

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