Acetyl chloride → HCID 20536188, compound

HRID 444083Notes

Reaction equation

HRID 444083 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:14])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1.C(N(CC)CC)C>C(OCC)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][C:1](=[O:3])[CH3:2])[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Product 1

HCID 20536188HCID 20536188, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Acetyl chloride (2.0 g) in diethyl ether (10 ml) was added dropwise to a stirred, cooled solution of 5-bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (5.0 g), prepared as in Example 5(e), and triethylamine (2.5 g) in diethyl ether (40 ml). After stirring for 3 hours at room temperature the mixture was washed with water three times, dried over magnesium sulphate and run down to yield 5 g of crude product, mp 73°-80° C., which was recrystallised from petroleum ether (80°-100° C.) with charcoaling to give 4 g of pure product, mp 83°-85° C.

Workup

  1. temperaturecooled
  2. washwas washed with water three times
  3. dry with materialdried over magnesium sulphate
  4. customto yield 5 g of crude product, mp 73°-80° C., which
  5. customwas recrystallised from petroleum ether (80°-100° C.) with charcoaling

Sources & evidence

ORD record
ord-63f5ec25e4c64b68bc4a86ff9509cb22
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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