2,4-Difluoroacetophenone → HCID 21099384, compound

HRID 1351686Notes

Reaction equation

HRID 1351686 reaction equation
FC1C=CC=CC=1C=[O:5].[Na].[BH4-].[Na+].Br[C:14](O)([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[C:39](=[O:41])[CH3:40]>>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[C:39](=[O:41])[CH2:40][C:27]1[CH:26]=[CH:25][C:24]([S:21]([C:14]2[CH:15]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][OH:5])(=[O:22])=[O:23])=[CH:29][CH:28]=1

Participants

6

Reactant 5

HCID 677702,4-DifluoroacetophenoneHCID 67970o-FluorobenzaldehydeHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 68534518HCID 68534518, compound

Product 1

HCID 21099384HCID 21099384, compound

Procedure

2-Fluorobenzaldehyde was reacted with sodium 4-bromophhenylsulfinate by the procedure of Example 113 Step 1, then the aldehyde group reduced using sodium borohydride by the procedure of Example 41. The resulting bromophenylsulfonylbenzyl alcohol was reacted with 2′,4′-difluoroacetophenone as described in Example 132 to provide the title compound. δH (500 MHz, d6 DMSO): 8.07 (1H, d, J=7.8 Hz), 7.96 (1H, q, J=8.0 Hz), 7.82–7.77 (3H, m), 7.72 (1H, t, J=7.5 Hz), 7.54 (1H, t, J=7.5 Hz), 7.48 (2H, d, J=8.2 Hz), 7.45–7.41 (1H, m), 7.23 (1H, td, J=2.2, 7.7 Hz), 5.41 (1H, t, J=5.7 Hz), 4.69 (2H, d, J=5.7 Hz), 4.45 (2H, s).

Sources & evidence

ORD record
ord-e3c0dfb51b20470fbc35a75ed6faa5b0
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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