N-bromobutanimide → 2-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

HRID 1710001Notes

Reaction equation

HRID 1710001 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([Cl:10])[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[Br:15]N1C(=O)CCC1=O>C(Cl)Cl>[OH:1][C:2]1[C:9]([Br:15])=[C:8]([Cl:10])[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 230354272-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

Product 1

HCID 230354152-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehydeYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.84 g (8.65 mmol) of 2-hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde and 1.85 g (10.4 mmol) of N-bromosuccinimide in 30 ml of methylene chloride was stirred overnight at ambient temperature. The solvent was evaporated and the residue was partitioned between water and hexane. The organic phase was dried and evaporated. The residue was chromatographed on 150 g of silica gel using a gradient from 1:99 to 5:95 (v/v) of ether:hexane as eluent. There was obtained 2.05 g (7.03 mmol, 81%) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde after crystallization from hexane; mp 92°-94° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between water and hexane
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe residue was chromatographed on 150 g of silica gel using a gradient from 1:99 to 5:95 (v/v) of ether

Sources & evidence

ORD record
ord-38bcc792b31a469d9451ae6b9a8e20c8
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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