Diethylcarbamoyl chloride → HCID 68380072, compound

HRID 2178719Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10]([N:12]([CH2:16][CH3:17])[C:13](Cl)=[O:14])[CH3:11]>>[CH2:10]([N:12]([CH2:16][CH3:17])[C:13](=[O:14])[O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:11]

Participants

Reactant 2

HCID 6916Diethylcarbamoyl chloride

HCID 757903-Chloro-4-fluorophenol

Product 1

HCID 68380072HCID 68380072, compound

Procedure

3-Chloro-4-fluorophenol was acylated with diethylcarbamoyl chloride to produce 3-chloro-4-fluorophenyl diethylcarbamate, which was converted to 3-chloro-4-fluoro-2-iodophenyl diethylcarbamate via ortho-metalation followed by treatment with iodine. Basic hydrolysis provided 3-chloro-4-fluoro-2-iodophenol, which was coupled to (2-hydroxyphenyl)boronic acid under Suzuki conditions to give 6-chloro-5-fluorobiphenyl-2,2′-diol. Copper-mediated cyclization provided 4-fluorodibenzo[b,d]furan-1-ol.

Sources & evidence

ORD record: ord-c23b641153ca4ff2980fae811f10461e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067934B2

Reaction notes

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