Bromide ion → HCID 18929208, compound

HRID 1599847Notes

Reaction equation

[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH2:12])[CH:3]=1.CN(C=O)C.[Br:18][CH2:19][C:20](Br)=[O:21].[Br-]>O1CCOCC1>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:20](=[O:21])[CH2:19][Br:18])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4,5-difluoro-2-aminobenzoic acid (20.0 g, 115.5 mmol) in a mixture of anhydrous DMF (50 mL) and anhydrous dioxane (50 mL) was cooled to 0° C. under N2 using an ice-bath. Bromoacetyl bromide (23.3 g, 10.1 mL, 115.5 mmol) was added dropwise, keeping the internal temperature between 0° and 5° C. over a 3/4 h period. After the addition of bromide was completed, the solution was warmed to rt, stirred overnight, and then the solution was slowly poured into 200 mL of ice-water. The resulting precipitate was filtered, washed with water, and then dried in a vacuum desiccator overnight to afford 31.24 g (92%) of the title compound as a white solid, mp 177°-180° C.: 1H NMR (DMSO-d6) δ14.17 (bs, 1H), 11.66 (s, 1H), 8.47 (dd, J=13.6, J=7.6, 1H), 7.97 (dd, J=11.2, J=9.2, 1H), 4.28 (s, 2H); 13C NMR (DMSO-d6) δ167.55, 165.45, 151.99 (dd, J=249, J=12.9), 144.53 (dd, J=242, J=12.9), 137.58 (dd, J=7.5, 1=3), 119.75 (d, J=18.9), 114.18 (t, J=3), 108.96 (d, J=23.5), 30.43; MS (EI m/z) 293 (M+).

Workup

customthe internal temperature between 0° and 5° C.
customover a 3/4 h
temperaturethe solution was warmed to rt
filtrationThe resulting precipitate was filtered
washwashed with water
customdried in a vacuum desiccator overnight

Sources & evidence

ORD record: ord-0cb53b63ae2a485f95b72e2a2062efce
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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