Water → HCID 23035426, compound

HRID 1710004Notes

Reaction equation

HRID 1710004 reaction equation
[CH3:1][C:2]([C:5]1[C:6]([O:15][CH3:16])=[CH:7][C:8]([OH:14])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:4])[CH3:3].[Br:17]Br.O>C(Cl)Cl>[Br:17][C:7]1[C:8]([OH:14])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 23035424HCID 23035424, compound

Product 1

HCID 23035426HCID 23035426, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.7 g (48.1 mmol) of 1-[5-(1,1-dimethylethyl)-2-hydroxy-4-methoxyphenyl]ethanone in 250 ml of methylene chloride was added 8.11 g (50.7 mmol) of bromine. The reaction mixture was stirred at ambient temperature for 2 hours. Water (500 ml) was added. The organic phase was separated, washed with saturated aqueous sodium bicarbonate, dried and evaporated. The residue was filtered through 150 g of silica gel using 10:90 (v/v) ether:hexane as eluent. There was obtained 8.70 g (28.8 mmol, 60%) of 1-[3-bromo-5-(1,1-dimethylethyl)-2-hydroxy-4-methoxyphenyl]ethanone as white crystals after crystallization from hexane; mp 69°-71° C.

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customdried
  4. customevaporated
  5. filtrationThe residue was filtered through 150 g of silica gel using 10:90 (v/v) ether

Sources & evidence

ORD record
ord-6187b1ba073a47a59a898733350558a6
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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