Water → HCID 86625614, compound

HRID 14483Notes

Reaction equation

HRID 14483 reaction equation
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[C:23]([OH:30])=[CH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])([CH3:4])([CH3:3])[CH3:2].[Br:33]N1C(=O)CCC1=O.O>ClCCl>[Br:33][CH:24]([C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[C:23]([C:8]1[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:12][C:7]=1[O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:32])[CH3:31])=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 687050871-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-phenyl]-1-hydroxy-4-methyl-pent-1-en-3-one

Product 1

HCID 86625614HCID 86625614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-phenyl]-1-hydroxy-4-methyl-pent-1-en-3-one (5.81 g, 12.72 mmol) is dissolved in dry dichloromethane (100 ml) at room temperature. N-bromosuccinimide (2.38 g, 13.36 mmol) is added portionwise. The reaction mixture is stirred at room temperature for 30 minutes, poured into water (200 ml) and extracted with dichloromethane (3×75 ml). The dichloromethane extracts are combined, washed with saturated brine (100 ml), dried (MgSO4), filtered and evaporated to give a pale yellow solid.

Workup

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washwashed with saturated brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a pale yellow solid

Sources & evidence

ORD record
ord-9dbbd1fe89e54bb6bbdbb7d90894bb2c
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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