Boron tribromide → HCID 59205819, compound

HRID 1678562Notes

Reaction equation

HRID 1678562 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][C:9]=2[O:16]C)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[OH:16])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59205888HCID 59205888, compound2×

Product 1

HCID 59205819HCID 59205819, compound

Procedure

Reaction Scheme 5 illustrates the synthesis of 4-(4-Iodophenyl)resorcinol (31). 2,4-Dimethoxyphenylboronic acid and 1-bromo-4-nitrobenzene in the presence of tetrakis(triphenylphosphine) palladium yielded 4-(4-nitrophenyl)-2,4-methoxybenzene (28). Hydrogenation of 28 in the presence of a palladium catalyst yielded the crude amine (29) which without purification was diazotized and treated with KI solution to yield the desired 4-(4-iodophenyl-2,4-dimethoxybenzene (30). The dimethoxy analog (30) was treated with boron tribromide to yield the desired 4-(4-iodophenyl)resorcinol (31).

Workup

  1. customwithout purification
  2. additiontreated with KI solution
  3. customto yield the

Sources & evidence

ORD record
ord-1a708f8041094f8cb1a447dd5a54212b
Source dataset
uspto-grants-2011_08
Patent number
US08008522B2

Reaction notes

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