3-Bromo-5-formylbenzoic acid → 3-Formyl-5-propyl-benzoic acid

HRID 1958804Notes

Reaction equation

HRID 1958804 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10](Br)[CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].[Br-].[CH2:14]([Zn+])[CH2:15][CH3:16]>>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2]

Participants

3

Reactant 2

HCID 223207963-Bromo-5-formylbenzoic acidHCID 178455869HCID 178455869, compound

Product 1

HCID 866505083-Formyl-5-propyl-benzoic acid

Procedure

The title compound is prepared in analogy to 3-formyl-5-ethyl-benzoic (582 mg) from 3-formyl-5-bromo-benzoic acid (1.00 g, 4.37 mmol) using propyl zinc bromide. LC-MS*: tR=0.56 min, [M−H]−=191.32; 1H NMR (D6-DMSO): δ 0.91 (t, J=7.3 Hz, 3H), 1.65 (h, J=7.3 Hz, 2H), 2.73 (t, J=7.3 Hz, 2H), 7.97 (s, 1H), 8.07 (s, 1H), 8.28 (s, 1H), 10.07 (s, 1H).

Sources & evidence

ORD record
ord-524bfddec0a941db9e7c34cf8468174b
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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