Formic Acid → N-(3-Bromophenyl)formamide

HRID 1358133Notes

Reaction equation

HRID 1358133 reaction equation
[CH:1]([OH:3])=O.CC(OC(C)=O)=O.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][CH:1]=[O:3])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 115623-Bromoaniline

Product 1

HCID 14272150N-(3-Bromophenyl)formamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of formic acid (24.3 g, 98%, 528 mmol) in Ac2O (43.94 g, 430 mmol) was heated to 55° C. for 2 hours, cooled to room temperature. The mixture was diluted with toluene (25 mL) followed by the addition of of 3-bromoaniline (28 g, 163 mmol) in toluene (40 mL). The solution was stirred cold for 30 minutes after which the solvents were removed under vacuo and the residue crystallized from hexane to give N-(3-bromophenyl)formamide (32.79 g). The material was added in portions to 1M. BH3 in THF (450 mL) at 0° C., heated to refluxing for 3 hours and cooled to ambient temperature. The solvents were removed under reduced pressure, the residue was treated with aqueous hydrochloric acid (1M, 200 mL) for for ½ hour, the pH was adjusted to 12 with the addition of sodium hydroxide (1M). The solution was extracted with diethyl ether (3×75 mL), the combined ether layers dried (MgSO4, filtered and concentrated under reduced pressure to give the titled compound (29.48).

Workup

  1. customwere removed under vacuo
  2. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-606e2caa04dc4352b5b486f1627ff985
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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