Ethyl orthoformate → 1-Bromo-2-(diethoxymethyl)benzene

HRID 2292161Notes

Reaction equation

HRID 2292161 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[CH:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])OCC>C(O)C.[Cl-].[NH4+]>[CH2:18]([O:17][CH:10]([O:14][CH2:15][CH3:16])[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1])[CH3:19]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 811292-Bromobenzaldehyde

Product 1

HCID 34827781-Bromo-2-(diethoxymethyl)benzeneYield 66.7%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-bromobenzaldehyde (33.2 g), triethyl orthoformate (29 g) and powdered ammonium chloride (0.379 g) in ethanol (30 ml) was stirred for eight hours at room temperature. The resulting suspension was filtered and the filtrate evaporated. The resulting yellow oil was distilled at reduced pressure to give the title compound (31 g). b.p. 63° C. 0.3 mm Hg. T.l.c. (Petrol/diethyl ether, 6:1) Rf=0.6.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate evaporated
  3. distillationThe resulting yellow oil was distilled at reduced pressure

Sources & evidence

ORD record
ord-b318e7806eea4d2a81958b67e9c632d1
Source dataset
uspto-grants-1989_01
Patent number
US04801599

Reaction notes

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