Water → HCID 19861819, compound

HRID 1165444Notes

Reaction equation

HRID 1165444 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([Cl:14])[C:3]=1[CH:4]=[O:5].[Br:15]N1C(=O)CCC1=O.O>C(Cl)Cl>[OH:1][C:2]1[C:9]([Br:15])=[CH:8][C:7]([C:10]([CH3:11])([CH3:13])[CH3:12])=[C:6]([Cl:14])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 19861825HCID 19861825, compound

Product 1

HCID 19861819HCID 19861819, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.97 g (9.26 mmol) of 2-hydroxy-5-(1,1-dimethylethyl)-6-chlorobenzaldehyde and 1.98 g (11.1 mmol) of N-bromosuccinimide in 30 ml of methylene chloride was stirred for 2 hours. Water (50 ml) was added. The organic phase was dried and evaporated. The residue was chromatographed on 150 g of silica gel eluted with 1:99 (v/v) ether:hexane. There was obtained 2.69 g (9.22 mmol, 99%) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)-6-chlorobenzaldehyde as a white solid after recrystallization from hexane; mp 103°-105° C.

Workup

  1. customThe organic phase was dried
  2. customevaporated
  3. customThe residue was chromatographed on 150 g of silica gel
  4. washeluted with 1:99 (v/v) ether

Sources & evidence

ORD record
ord-ef01c064c9a84ba6aeefdb939477e7f4
Source dataset
uspto-grants-1990_03
Patent number
US04910202

Reaction notes

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