Iodine → HCID 68379967, compound

HRID 2178720Notes

Reaction equation

HRID 2178720 reaction equation
C(N(CC)C(=O)[O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([Cl:13])[C:7]=1[I:14])C.II>>[Cl:13][C:8]1[C:7]([I:14])=[C:6]([OH:5])[CH:11]=[CH:10][C:9]=1[F:12]

Participants

3

Reactant 2

HCID 807IodineHCID 68380495HCID 68380495, compound

Product 1

HCID 68379967HCID 68379967, 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.

Workup

  1. customBasic hydrolysis

Sources & evidence

ORD record
ord-5e2364066a24438583f4872849a0a94e
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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