2-Bromophenol → 2-Bromo-4-thiocyanatophenol

HRID 858148Notes

Reaction equation

[Pb](SC#N)[S:2][C:3]#[N:4].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15]>C(Cl)Cl>[Br:8][C:9]1[CH:14]=[C:13]([S:2][C:3]#[N:4])[CH:12]=[CH:11][C:10]=1[OH:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lead thiocyanate (6.49 g, 20.05 mmol) in CH2Cl2 (125 mL) under nitrogen at 0° C. PhICl2 (4.41 g, 16.05 mmol) was added in one portion. After 20 min at 0° C. a solution of 2-bromophenol (2.31 g, 1.55 mL, 13.37 mmol) in CH2Cl2 (10 mL) was added. After stirring the mixture for 45 min at 0° C. the salts were filtered and the solvent evaporated. The crude mixture was purified by silica gel flash chromatography (hexane-EtOAc 5:1→2:1) to yield 1 (2-bromo4-thiocyanatophenol) (1031 mg, 33%) as a pale yellow oil.

Workup

additionPhICl2 (4.41 g, 16.05 mmol) was added in one portion
filtrationwere filtered
customthe solvent evaporated
customThe crude mixture was purified by silica gel flash chromatography (hexane-EtOAc 5:1→2:1)

Sources & evidence

ORD record: ord-607b569c7a10488e94e5181d68f2ea60
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148236B2

Reaction notes

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