Dimethylformamide → 4-(Benzyloxy)-2-fluorobenzaldehyde

HRID 1394713Notes

Reaction equation

HRID 1394713 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[F:16].[Li]CCCC.CN(C)[CH:24]=[O:25]>O1CCCC1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:24]=[O:25])=[C:3]([F:16])[CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 222739334-(Benzyloxy)-1-bromo-2-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 121369894-(Benzyloxy)-2-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 8 c], 1-bromo-2-fluoro-4-(phenylmethoxy)-benzene was treated with n-BuLi and N,N-dimethylformamide in dry tetrahydrofuran to yield 4-benzyloxy-2-fluoro-benzaldehyde as off-white crystals.

Sources & evidence

ORD record
ord-1b9b16313fbf417987b0ede5454431d6
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

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