2-Bromo-5-methoxybenzaldehyde → HCID 18377949, compound

HRID 2298723Notes

Reaction equation

HRID 2298723 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.FC(F)(F)O[C:29]1C=CC(Br)=C[CH:30]=1>>[CH:4]([C:3]1[CH:6]=[C:7]([O:10][CH2:11][CH2:29][CH3:30])[CH:8]=[CH:9][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([O:14][C:13]([F:25])([F:24])[F:12])=[CH:16][CH:17]=1)=[O:5]

Participants

4

Reactant 3

HCID 3444802-Bromo-5-methoxybenzaldehydeHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 18377949HCID 18377949, compound

Procedure

Similarly to the method described by Kumar, S., J.Org.Chem. 62, 8535 (1997), 2-bromo-5-methoxy-benzaldehyde (for preparation see Ex. 1) and 4-trifluoromethoxyphenylboronic acid {prepared in a conventional manner from 4-trifluoromethoxy-bromobenzene [407-14-7]} are reacted to give 2-formyl-4-propyloxy-4′-trifluoromethoxy-biphenyl. Similarly to the method described in the same reference, this compound is reacted with trimethylsulfonium iodide under phase transfer conditions to give the corresponding oxiranyl derivative which can be isolated, but can alternatively advantageously be directly converted into the target compound by reaction with methanesulfonic acid (as described by Kumar, loc. cit.). Aqueous workup can be followed by purification as described in Ex. 1.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-dd7cb7a3bbe749a08c44a217d5fd5d57
Source dataset
uspto-grants-2002_12
Patent number
US06495220B2

Reaction notes

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