Chloroform → HCID 14856379, compound

HRID 1089564Notes

Reaction equation

HRID 1089564 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([OH:17])=[C:11]([CH2:18][CH:19]=[CH2:20])[C:10]=1[CH3:21])(=[O:7])[CH3:6].[Br:22]Br>C(N(CC)CC)C>[C:5]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]2[O:17][CH:19]([CH2:20][Br:22])[CH2:18][C:11]=2[C:10]=1[CH3:21])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 15086715HCID 15086715, compound

Product 1

HCID 14856379HCID 14856379, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a chloroform (15 ml) solution of 4-acetoxy-2-allyl-3,5,6-trimethylphenol [2.0 g (8.5 mmol)] was added dropwise while stirring, bromine [1.36 g (8.5 mmol)]. To the mixture was then added triethylamine (0.3 ml), which was heated for two hours under reflux. The reaction mixture was cooled, washed with water, dried and then concentrated. The concentrate was crystallized from hexane to obtain 5-acetoxy-2-bromomethyl-4,6,7-trimethyl-2,3-dihydrobenzofuran [2.5 g (yield 93.2%)].

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe concentrate was crystallized from hexane

Sources & evidence

ORD record
ord-3ac29ecb5de74483a2c98b0ed2027f39
Source dataset
uspto-grants-1990_10
Patent number
US04966973

Reaction notes

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