4-Iodoanisole → HCID 10518841, compound

HRID 1077091Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].I[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

Reactant 2

HCID 696764-Iodoanisole

HCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 10518841HCID 10518841, compound

Procedure

2,5-Dibromo-1-nitrobenzene and 4-iodoanisole were reacted under Ullmann conditions to give 4-bromo-4'-methoxy-2-nitrobiphenyl, m.p. 130°-131°C. This was reduced to give 2-amino-4-bromo-4'-methoxybiphenyl, m.p. 128°-130°C., which was subjected to the Schiemann reaction using hydrofluoroboric acid to give the product, b.p. 134°-138°C./0.15mm.

Sources & evidence

ORD record: ord-ba3baeee5ea4437b99ce2dfd7253038e
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03959364

Reaction notes

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