Dimethylformamide → HCID 49842931, compound

HRID 40172Notes

Reaction equation

HRID 40172 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:5]([Br:15])=[CH:4][C:3]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C([Li])CCC.CN(C)[CH:30]=[O:31]>>[Br:15][C:5]1[C:6]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:2]([CH:30]=[O:31])=[C:3]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 49842932(2,5-Dibromo-1,4-phenylene)bis(hexylsulfane)HCID 178418339Butyllithium

Product 1

HCID 49842931HCID 49842931, compoundYield 50%

Procedure

BrS6 was converted to BrS6A by the same methods as Br6A and BrC6A, using butyllithium and dimethylformamide. Products were purified by column chromatography with ethylacetate:hexane (1:30) eluent followed by recrystallization from methanol. Yellow powder is collected at a yield of 50%. For BrS6A, 1H NMR (500 MHz, CDCl3): δ 10.39 (s 1H), 7.64 (s 1H), 7.61 (s 1H), 3.00 (t 2H), 2.91 (t 2H), 1.73-1.65 (m 4H), 1.46 (m, 4H), 1.34-1.28 (m 8H), 0.89 (m 6H).

Workup

  1. customProducts were purified by column chromatography with ethylacetate:hexane (1:30) eluent
  2. customfollowed by recrystallization from methanol
  3. customYellow powder is collected at a yield of 50%

Sources & evidence

ORD record
ord-d4672499a37f43a88a83464cb1962b88
Source dataset
uspto-grants-2013_09
Patent number
US08525131B2

Reaction notes

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