Water → HCID 68431145, compound

HRID 2267006Notes

Reaction equation

HRID 2267006 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:18]=1[C:31]([F:34])([F:33])[F:32])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN(C)C=O>[CH2:24]([O:23][C:19]1[CH:20]=[CH:21][C:22]([Br:1])=[C:17]([O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:18]=1[C:31]([F:33])([F:32])[F:34])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68430768HCID 68430768, compound

Product 1

HCID 68431145HCID 68431145, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add N-bromosuccinimide (4.67 g, 26.23 mmol) to a solution of 1,3-bis-benzyloxy-2-trifluoromethyl-benzene (9.40 g, 26.2 mmol) in dimethylformamide (100 mL) and stir. After 18 hours add water and extract with diethyl ether. Combine organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title compound as an orange oil (11.20 g, 98%): 1H NMR (CD3CN) δ 4.97 (2, 2H), 5.18 (s, 2H), 6.99 (d, 1H), 7.33-7.55 (m, 10H), 7.79 (d, 1H).

Workup

  1. extractionextract with diethyl ether
  2. dry with materialCombine organic layers, dry with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e481ef0d712f48108aad3fb097d2f3ee
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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