Chlorotrimethylsilane → HCID 15434957, compound
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](Cl)(C)C.[CH2:16]([C:19]1[CH:40]=[C:39]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:37][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:28][CH:27]=1)[CH2:17][CH3:18].[Br:48]N1C(=O)CCC1=O>C1COCC1>[Br:48][CH:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:20]2[CH:37]=[CH:38][C:39]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:40][C:19]=2[CH2:16][CH2:17][CH3:18])=[CH:27][CH:28]=1)[C:33]([O:35][CH3:36])=[O:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of lithium bis(trimethylsilyl)amide (27.36 mL, 27.36 mmol) in dry THF (80 mL) was treated with trimethylsilyl chloride (5.94 mL, 46.76 mmol) at -78° C. To this mixture was added dropwise a solution of the product of Step B (10.80 g, 24.87 mmol) in THF (15 mL). The reaction mixture was stirred at -78° C. for 2 h. N-bromosuccinimide (4.65 g, 26.12 mmol) was added, and the mixture was allowed to warm to room temperature overnight. THF was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed once with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to provide methyl α-bromo-4-(3-(2-propyl-4-phenoxy-phenoxy)propoxy)phenylacetate as an oil.
Workup
- temperatureto warm to room temperature overnight
- customTHF was evaporated
- customthe residue was partitioned between ethyl acetate and water
- washThe organic layer was washed once with water
- dry with materialdried over sodium sulfate
- filtrationThe organic layer was filtered
- customevaporated
Sources & evidence
- ORD record
- ord-94418554259e4a88b0dfccf5b3b8eda9
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008237
Reaction notes
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