Toluene → HCID 86722663, compound

HRID 1480437Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:10][OH:11])[CH:9]=1)[C:5]#[N:6].[C:12](Cl)([Cl:14])=[O:13].C1(C)C=CC=CC=1>C1COCC1>[C:12]([Cl:14])(=[O:13])[O:11][CH2:10][C:8]1[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=1

Participants

Conditions

Temperature: 10 °C

Procedure

3-Chloro-5-(hydroxymethyl)benzonitrile (25 g, 145 mmol) was dissolved in THF (200 mL). The resulting yellow solution was cooled to 10° C. in an ice bath and treated dropwise with phosgene in toluene (152 mL, 289 mmol). The reaction mixture was stirred at ambient temperature for 16 hrs. The mixture was concentrated under reduced pressure and the crude material was diluted with toluene (200 ml) and re-concentrated under reduced pressure. The residue was purified by chromatography on silica (Redisep 340 g column on a Biotage system), eluting with EtOAc/iso-hexane to give 3-chloro-5-cyanobenzyl carbonochloridate as an oil.

Workup

concentrationThe mixture was concentrated under reduced pressure
additionthe crude material was diluted with toluene (200 ml)
concentrationre-concentrated under reduced pressure
customThe residue was purified by chromatography on silica (Redisep 340 g column on a Biotage system),
washeluting with EtOAc/iso-hexane

Sources & evidence

ORD record: ord-1e8db2fd8a414b3f82f804189bc1cab9
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409895B2

Reaction notes

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