Water → HCID 22152298, compound

HRID 1111335Notes

Reaction equation

HRID 1111335 reaction equation
[OH:1][C:2]1[C:12]([CH:13]=[O:14])=[CH:11][C:5]2[C:6]([CH3:10])([CH3:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[Br:15]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:15][C:3]1[C:4]2[O:8][CH2:7][C:6]([CH3:10])([CH3:9])[C:5]=2[CH:11]=[C:12]([CH:13]=[O:14])[C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22152291HCID 22152291, compound

Product 1

HCID 22152298HCID 22152298, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.27 g (27.4 mmol) of 2,3-dihydro-6-hydroxy-3,3-dimethyl-5-benzofurancarboxaldehyde and 5.86 g (32.9 mmol) of N-bromosuccinimide in 135 ml of methylene chloride was stirred at ambient temperature for 3 h. Water (400 ml) was added. The organic phase was dried and evaporated. The residue was chromatographed on silica gel (150 g) using a gradient from 20:80 (v/v) ether:hexane to 40:60 (v/v) ether:hexane eluent. There was obtained 7.0 g (25.8 mmol, 94%) of 7-bromo-2,3-dihydro-6-hydroxy-3,3-dimethyl-5-benzofurancarboxaldehyde. A sample was crystallized from toluene: mp 152°-154° C.

Workup

  1. customThe organic phase was dried
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (150 g)

Sources & evidence

ORD record
ord-a4dc9596978f4a82be6507a694c1b00a
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

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