3-Bromo-4-(trifluoromethoxy)benzaldehyde → 3-(5-Hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde

HRID 460298Notes

Reaction equation

HRID 460298 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6]2[CH:7]=[C:8]([CH2:20][OH:21])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:5]=2[O:4][CH2:3]1.Br[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=[O:28]>>[OH:21][CH2:20][C:8]1[CH:9]=[C:10]([C:30]2[CH:29]=[C:26]([CH:25]=[CH:24][C:31]=2[O:32][C:33]([F:34])([F:35])[F:36])[CH:27]=[O:28])[C:5]2[O:4][CH2:3][C:2]([CH3:1])([CH3:22])[C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 131504163-Bromo-4-(trifluoromethoxy)benzaldehydeHCID 18445402[3,3-Dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-methanol

Product 1

HCID 184454093-(5-Hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehydeYield 59%

Procedure

The intermediate 3-(5-hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde was prepared in a similar manner to example 1a using [3,3-dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-methanol and 3-bromo-4-trifluoromethoxy benzaldehyde. 59% yield. 1H-NMR (300 MHz, CDCl3): 1.39 (s, 6H), 1.71 (m, 1H), 4.26 (s, 2H), 4.68 (s, 2H), 7.14 (d, J=2.3 Hz, 1H), 7.21 (d, J=1.5 Hz, 1H), 7.49 (dd, J1=8.5 Hz, J2=1.5 Hz, 1H), 7.91 (dd, J1=8.5 Hz, J2=2.1 Hz, 1H), 8.01 (d, J=2.3 Hz, 1H), 10.03 (s, 1H).

Sources & evidence

ORD record
ord-2445a4763310420490e249d0bd62c384
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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