Benzaldehyde → HCID 54135330, compound

HRID 1743470Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9](I)[C:8]([O:12][CH2:13][O:14][CH3:15])=[C:7](Br)[CH:6]=1)[CH3:2].C(O[C:21](=[O:34])[C:22]1[CH:27]=[C:26](Br)[C:25](OCOC)=[C:24](Br)[CH:23]=1)C.[CH:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:38]2[CH:39]=[CH:40][CH:41]=[C:36]([CH:35]=[O:42])[CH:37]=2)[C:8]([O:12][CH2:13][O:14][CH3:15])=[C:7]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:21]=[O:34])[CH:27]=2)[CH:6]=1)[CH3:2]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 54265004HCID 54265004, compound

HCID 54329281HCID 54329281, compound

Product 1

HCID 54135330HCID 54135330, compound

Procedure

3,5-Bis-(3-formylphenyl)-4-methoxymethoxybenzoic acid ethyl ester was prepared as a white solid (980 mg, 13.7%) in a similar manner to Step 1 of Example 143 from a 2:1 mixture of 3-bromo-4-methoxymethoxy-5-iodobenzoic acid ethyl ester and 3,5-dibromo-4-methoxymethoxybenzoic acid ethyl ester. There also yielded 1.6 g of a mixture of benzaldehyde and the starting halogenated compound, and 1.4 g, 20.7% of the monoarylated material as a white solid. Bis-arylated compound: 1H NMR (CDCl3) δ 1.38 (t, J=7.36 Hz, 3H); 2.59 (s, 3H); 4.33–4.42 (m, 4H); 7.62 (t, J=7.36 Hz, 2H); 7.79 (dd, J=8.18 Hz, 2.05 Hz, 4H); 7.97 (s, 2H); 8.02 (s, 2H); 10.11 (s, 2H). Mono-arylated compound: 1H NMR (CDCl3) δ 1.38 (t, J=8.18 Hz, 3H); 3.06 (s, 3H); 4.37 (quartet, J=8.18 Hz, 2H); 4.80 (s, 2H); 7.60 (t, J=7.36 Hz, 1H); 7.77–7.82 (m, 1H); 7.87–7.91 (m, 1H); 7.96–8.00 (m, 1H); 8.01–8.06 (m, 1H); 8.26–8.30 (m, 1H).

Sources & evidence

ORD record: ord-216114bc1e364439aaa6345ff12efa83
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008636B2

Reaction notes

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