Bromine → HCID 131713376, compound
Reaction equation
[Br:1]Br.[C:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH:14]=[CH2:15])(=[O:5])[CH3:4]>C(=S)=S>[Br-:1].[Br-:1].[C:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH:14]=[CH2:15])(=[O:5])[CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of bromine (90 g) in carbon disulphide (100 ml) was added dropwise to a well stirred solution of O-acetyl-2-allylphenol (100 g) in carbon disulphide (300 ml) at -10° C. over 1 hour. The solution was evaporated to dryness in vacuo, to afford O-acetyl-2-allylphenol dibromide which was immediately dissolved in dry ethanol (300 ml) containing 10 ml of a saturated ethanolic-hydrogen chloride solution. The solution was heated under gentle reflux for 2 hours, and then evaporated to dryness in vacuo. The residue was triturated with n-pentane, and the solid 2-allylphenol dibromide (135 g) was collected and washed twice with portions of n-pentane. The product is pure enough for further reaction. 2-Allylphenol dibromide (135 g) in dry ethanol (300 ml) was treated with a solution of sodium ethoxide (38 g) in ethanol (100 ml) with cooling and stirring, keeping the temperature of the reaction between 30° and 35° C. After addition, the reaction was stirred at room temperature for 1 hour, and then evaporated to dryness in vacuo. The residue was partioned between n-pentane and water. The n-pentane fraction was washed with 2% sodium hydroxide solution, water, and dried (Na2SO4). Evaporation to dryness in vacuo afforded crude (2,3-dihydro-2-benzofuranyl)-methyl bromide (90 g), which distilled at 110°-118° C./0.5 mm to afford product (78 g) of slightly higher purity.
Workup
- customThe solution was evaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-8eb7e7ddb4df464883f52b81e7c9f113
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04428940
Reaction notes
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