Bromobenzene → HCID 61100383, compound

HRID 2378188Notes

Reaction equation

COC1C=C(C=C(OC)C=1)C=O.BrC1C=CC=CC=1.C([Li])CCC.O1[C:30]2[CH:31]=[CH:32][C:33]([CH:35]([C:37]3[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=3)[OH:36])=[CH:34][C:29]=2OCC1>>[CH3:46][O:45][C:39]1[CH:38]=[C:37]([CH:35]([C:33]2[CH:34]=[CH:29][CH:30]=[CH:31][CH:32]=2)[OH:36])[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=1

Participants

Reactant 4

HCID 7961Bromobenzene

HCID 817473,5-Dimethoxybenzaldehyde

HCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol

HCID 178418339Butyllithium

Product 1

HCID 61100383HCID 61100383, compoundYield 85%

Procedure

3,5-Dimethoxybenzaldehyde (2.50 g, 15.04 mmol), bromobenzene (2.60 g, 16.55 mmol), and n-butyl lithium (33.10 ml, 13.24 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.) to give (3,5-Dimethoxy-phenyl)-phenyl-methanol as a light yellow oil (3.14 g, 85%). HPLC purity was 83% at 3.01 min. (50/50 ACN/0.1% H3PO4). 1HNMR (CDCl3) δ 7.39-7.25 (m, 4H, Ar), 6.54 (d, J=2 Hz, 2H, Ar), 6.50-6.34(m, 2H, Ar), 5.74 (d, J=3 Hz, 1H, CHOH), 3.75 (s, 6H, 2OCH3), 2.34 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

customThe crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.)

Sources & evidence

ORD record: ord-ad2b3ca6df4c44389dad0c01634edb1e
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470723B2

Reaction notes

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