Water → HCID 69103680, compound

HRID 2220412Notes

Reaction equation

HRID 2220412 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.S(Cl)([Cl:19])=O.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Cl:19])=[C:4]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 69104144HCID 69104144, compound

Product 1

HCID 69103680HCID 69103680, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-2-cyclohexyloxyphenyl)methanol (5.46 g) in dichloromethane (16 ml) was added thionyl chloride (3.42 g) dropwise at 5° C. under nitrogen, and the mixture was stirred at the same temperature for 1.5 hours. The resulting mixture was poured into water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated and dried in vacuo to give 4-bromo-1-chloromethyl-2-cyclohexyloxybenzene (5.59 g).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-334253531e8f4a9e86318431248e6eb2
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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