3-Bromobenzaldehyde → HCID 67538669, compound

HRID 2240983Notes

Reaction equation

HRID 2240983 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[PH:10](=O)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>C(N(CC)CC)C>[CH2:12]([O:11][P:10]([CH:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)[OH:6])[O:14][CH2:15][CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 178476833HCID 178476833, compound

Product 1

HCID 67538669HCID 67538669, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Conditions

Temperature
40 °C

Procedure

Into a mixture of 3-bromobenzaldehyde (20 g, 108.1 mmol) and diethyl phosphonate (14.2 g, 108.1 mmol) was added triethylamine (0.44 g, 4.32 mmol) and the mixture was stirred at 40° C. for 72 hours. Purification by ISCO (hexane/EtOAc 1/1) gave diethyl[(3-bromophenyl)(hydroxy)methyl]phosphonite (32.62 g); MS m/e (M)+ 322.

Workup

  1. customPurification by ISCO (hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-83010bd766dc4bbfabff2d2fa224e08c
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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