Water → HCID 66738564, compound

HRID 1483616Notes

Reaction equation

HRID 1483616 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:6][C:3]=1[CH2:4][OH:5].C(N(C(C)C)CC)(C)C.[CH3:27][O:28][CH2:29]Cl.O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13])=[CH:6][C:3]=1[CH2:4][O:5][CH2:27][O:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 67310582HCID 67310582, compound

Product 1

HCID 66738564HCID 66738564, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-tert-butyldimethylsiloxybenzylalcohol (36.9 g, 116 mmol) and diisopropylethylamine (26.0 mL, 150 mmol) in dichloromethane (300 mL) was added chloromethyl methyl ether (11.0 mL, 145 mmol), and the mixture was stirred at room temperature for overnight. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (96:4 hexane/ethyl acetate) to give 1-bromo-4-tert-butyldimethylsiloxy-2-methoxymethoxymethylbenzene (39.3 g, 94%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (96:4 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-37c5463259fc42878996b6f158895486
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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