3-Bromotoluene → 4-(3-methylphenyl)benzaldehyde

HRID 1993098Notes

Reaction equation

HRID 1993098 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1>>[CH3:19][C:15]1[CH:14]=[C:13]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 115603-BromotolueneHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27598134-(3-methylphenyl)benzaldehyde

Procedure

Scheme 43, Example 1 depicts the coupling reaction of 4-formylbenzeneboronic acid 43.1 with 3-bromotoluene 43.9 to afford 3′-methylbiphenyl-4-aldehyde 43.10. The product is then reacted with N-bromosuccinimide, as described above, to afford the bromomethyl product 43.11. This material is reacted with a sodium dialkyl phosphonate 43.5 to afford the phosphonate ester 43.12.

Sources & evidence

ORD record
ord-a5124a7084b4415ba8fab8f0fec8de32
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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