3,5-Dimethoxybenzaldehyde → HCID 86596005, compound

HRID 2378192Notes

Reaction equation

HRID 2378192 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[O:6][C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[O:9][C:4]=2[CH:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1)[CH:21]=[O:22].C([Li])CCC.O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)O)=CC=2OCC1>>[CH3:27][O:26][C:24]1[CH:23]=[C:20]([CH:21]([C:3]2[C:4]3[O:9][C:8]([F:11])([F:10])[C:7]([F:13])([F:12])[O:6][C:5]=3[CH:14]=[CH:15][CH:2]=2)[OH:22])[CH:19]=[C:18]([O:17][CH3:16])[CH:25]=1

Participants

5

Reactant 4

HCID 817473,5-DimethoxybenzaldehydeHCID 27766116-Bromo-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxineHCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 86596005HCID 86596005, compoundYield 26.4%

Procedure

6-Bromo-2,2,3,3-tetrafluoro-2,3-dihydrobenzo[1,4]dioxine (1.50 g, 5.23 mmol), 3,5-dimethoxybenzaldehyde (0.79 g, 4.75 mmol), and n-butyl lithium (2.09 ml, 5.23 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 (5% EtOAc in hexane gradient to 30% EtOAc in hexane in about 40 min.) to give (3,5-Dimethoxy-phenyl)-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-5-yl)-methanol as an oil (0.47 g, 26%): 1HNMR (CDCl3) 7.37 (dd, J=1, 7 Hz, 1H, Ar), 7.17 (t, J=8 Hz, 1H, Ar), 7.06 (dd, J=1, 8 Hz, 1H, Ar), 6.57 (d, J=2 Hz, 2H, Ar), 6.38 (t, J=2 Hz, 1H, Ar), 6.12 (d, J=3 Hz, 1H, CHOH), 3.77 (s, 6H, 2OCH3), 2.36 (d, J =3 Hz, 1H, OH). The product was carried over to the next step.

Workup

  1. customThe crude material was purified via flash column chromatography (5% EtOAc in hexane gradient to 30% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record
ord-8ddea80d00b740ea8664cca056077f4b
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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