Water → HCID 19701607, compound

HRID 862057Notes

Reaction equation

HRID 862057 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7]O.C(N(CC)CC)C.CS([Cl:25])(=O)=O.O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7][Cl:25]

Participants

6

Procedure

To a solution of 5-bromo-2-methoxymethoxybenzyl alcohol (27.2 g) and triethylamine (23 ml) in dichloromethane (550 ml) was added, at 0° C., methanesulfonyl chloride (13.9 g). The mixture was stirred for 15 hours, while warming up to room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate), followed by concentration to give an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-2-methoxymethoxybenzyl chloride (21.6 g) as an oily product.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with an aqueous saline solution, which
  3. dry with materialwas then dried (anhydrous magnesium sulfate)
  4. concentrationfollowed by concentration
  5. customto give an oily product
  6. customThe oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-86398937883d410993a3db48e84943b9
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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