tert-Butyl methyl ether → Benzenamine, 2-bromo-6-fluoro-4-methyl-

HRID 919033Notes

Reaction equation

HRID 919033 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.CC(OC)(C)C.[Br:16]Br>O>[Br:16][C:6]1[CH:5]=[C:4]([CH3:9])[CH:3]=[C:2]([F:1])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 679842-Fluoro-4-methylaniline

Product 1

HCID 26598247Benzenamine, 2-bromo-6-fluoro-4-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
18 °C

Procedure

6-fluoro-4-methylaniline 6 (15 kg) was added to a mixture of MTBE (92 L, 66.6 kg) calcium carbonate (12 kg) and water (135 kg), inerted and cooled to <5° C. Bromine (18.22 kg) was charged, keeping T<10° C. Age for 30 minutes at T<10° C. The batch was warmed to ˜18° C. and allowed to settle.

Workup

  1. temperatureinerted and cooled to <5° C
  2. customT<10° C

Sources & evidence

ORD record
ord-d84c7d3fa8c142049cee2148e95d25ac
Source dataset
uspto-grants-2016_03
Patent number
US09272999B2

Reaction notes

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