Bromoacetyl bromide → HCID 19756863, compound

HRID 1588027Notes

Reaction equation

[NH2:1][C:2]1([F:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:3]1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[Br:17][CH2:18][C:19](Br)=[O:20]>ClCCl.O>[Br:17][CH2:18][C:19]([NH:1][C:2]1([F:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:3]1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])=[O:20]

Participants

Conditions

Temperature: -10 °C

Procedure

To a cooled (-10° C.), stirred suspension of 2-amino-2-fluorobenzophenone (19.40 g, 0.090 mol) in dichloromethane (130 mL) and water (10 mL) was added a solution of bromoacetylbromide (9.0 mL, 0.104 mol) in dichloromethane (30 mL), keeping the temperature of the reaction mixture at -10° C. After addition the reaction mixture was stirred whilst warming to room temperature (21/2hours). The organic layer was collected, washed with water (2×100 mL) then concentrated to approximately 70 mL. Hexane (70 mL) was added and the required product collected by filtration (25.6 g, 83%): mp 120°-121° C. Rf 0.30 in diethyl ether/n-hexane (1:1) on silica; 1H NMR (CDCl3) δ4.05 (2H,s), 7.10-7.64 (7H, m), 8.70 (1H, d, J=8 Hz), 11.95 (1H, broad s); MS, m/z 335 (M+ ). Anal. Calcd. for C15H11BrFNO2 :C, 53.59; H, 3.30; N, 4.17. Found: C, 53.32; H, 3.33; N, 4.00.

Workup

customat -10° C
additionAfter addition the reaction mixture
stirringwas stirred
temperaturewhilst warming to room temperature (21/2hours)
customThe organic layer was collected
washwashed with water (2×100 mL)
concentrationthen concentrated to approximately 70 mL
additionHexane (70 mL) was added
filtrationthe required product collected by filtration (25.6 g, 83%)

Sources & evidence

ORD record: ord-d9775c614e3446929fbfb47665fb1871
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05220018

Reaction notes

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