Hydrochloric Acid → 4-(4-Hydroxy-3-iodophenyl)benzonitrile

HRID 1167862Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].[I-:17].[OH-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][C:7]=1[I:17]

Participants

Conditions

Temperature: 0 °C

Procedure

4′-Hydroxy-1,1′-biphenyl-4-carbonitrile (25.0 g, 128 mmol), purchased commercially, NaI (19.19 g, 128 mmol), and sodium hydroxide (5.12g, 128 mmol) were combined in methanol (500 mL) at 0° C. and treated with bleach (5.25%, 181.0 g) dropwise over 1 hour. After stirring at 0° C. for 1 hour, the mixture was treated with 10% aqueous sodium thiosulfate (250 mL). The mixture was adjusted to pH 6.8 with 10% aqueous HCl and then the mixture was filtered. The filter cake was crystallized from hot CH2Cl2/hexane to provide the title compound (40% yield). 1HNMR (300 MHz, CDCl3) δ5.40 (s, 1H), 7.10 (m, 1H), 7.50 (m, 1H), 7.60 (m, 2H), 7.77(m, 2H), 7.90 (m, 1H); MS (CDI) m/z 339 (M+NH4)+.

Workup

additiontreated with bleach (5.25%, 181.0 g) dropwise over 1 hour
filtrationthe mixture was filtered
customThe filter cake was crystallized from hot CH2Cl2/hexane

Sources & evidence

ORD record: ord-c67ee7f6e36842c286e643e8fb38894d
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620839B2

Reaction notes

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