N,N-Dimethylaniline → [1,1'-Biphenyl]-4-yl carbonochloridate

HRID 1921605Notes

Reaction equation

HRID 1921605 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:14](Cl)([Cl:16])=[O:15].CN(C)C1C=CC=CC=1.O>C1(C)C=CC=CC=1.C(OCC)C.C1(C)C=CC=CC=1>[Cl:16][C:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:15]

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 6371PhosgeneHCID 71034-Hydroxybiphenyl

Product 1

HCID 15462084[1,1'-Biphenyl]-4-yl carbonochloridate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 22238780Ether tolueneSolvent

Procedure

4-Hydroxybiphenyl (2.62 g, 15.4 mmol) in absolute toluene/diethyl ether (60/30 mL) was added dropwise in the space of 30 minutes, with ice cooling, to a solution of phosgene (1.98 g, 20 mmol) in absolute toluene (20 mL). Then, at −3° C., N,N-dimethylaniline (1.86 g, 1.95 mL, 15.4 mmol) in absolute toluene (10 mL) was added dropwise and it was stirred overnight, while slowly warming to room temperature. After cooling to 0° C. again, water (30 mL) was slowly added dropwise, then the organic phase was washed with 0.1N HCl, 0.1N NaOH and water (each 2×100 mL), dried over sodium sulphate and concentrated under vacuum.

Workup

  1. temperatureAfter cooling to 0° C. again
  2. washthe organic phase was washed with 0.1N HCl, 0.1N NaOH and water (each 2×100 mL),
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-72f93d99ba204f1398dfddec3b2387b3
Source dataset
uspto-grants-2012_05
Patent number
US08173700B2

Reaction notes

Loading…