Dimethylformamide → HCID 11157507, compound

HRID 2087022Notes

Reaction equation

HRID 2087022 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[C:11]([Cl:23])[C:10]=1[O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:32]N1C(=O)CCC1=O.CN(C=O)C>O>[Br:32][C:12]1[C:13]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])=[C:10]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[C:11]=1[Cl:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 11168019HCID 11168019, compound

Product 1

HCID 11157507HCID 11157507, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0.650 g (1.30 mmol) of 14 and 0.276 g (1.60 mmol) of N-bromosuccinimide (NBS) in 10 Ml of DMF under argon was stirred at 25° C. for 5 days. The reaction mixture was diluted with 30 Ml of water, extracted three times with diethyl ether (50 Ml each), and the combined extracts were washed with 30 Ml of water, and 30 Ml of brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and diethyl ether as eluent gave 0.506 g (67% yield) of bromide 4. 1H NMR (CDCl3) δ 6.41 (s, 1H, Ar, C3-H), 1.03 (s, 9H, t-Bu), 1.02 (s, 9H, t-Bu), 0.97 (s, 9H, t-Bu), 0.23 (s, 6H, Me), 0.22 (s, 6H, Me), 0.18 (s, 6H, Me); 13C NMR (CDCl3) δ 147.3 (s), 147.2 (s), 139.4 (s), 128.3 (s), 111.1 (d), 108.4 (s), 29.9 (q, t-Bu), 26.3 (q, t-Bu), 26.2 (q), 26, 18.9 (s), 18.6 (s), −3.3 (q, Me), −3.4 (q, Me), −3.5 (q, Me), −4.0 (q). Anal. Calcd for C24H46BrClO3Si3: C, 49.51; H, 7.96. Found: C, 49.78; H, 8.11.

Workup

  1. extractionextracted three times with diethyl ether (50 Ml each), and the combined extracts
  2. washwere washed with 30 Ml of water, and 30 Ml of brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customcolumn chromatographed on silica gel using
  6. additiona gradient mixture of hexane and diethyl ether as eluent

Sources & evidence

ORD record
ord-90a7a41996da496fbfcb1620bb7b8855
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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